D-Biotin supplier | CasNO.58-85-5

Name
D-Biotin
EINECS 200-399-3
CAS No. 58-85-5
Article Data122
CAS DataBase
Density 1.267 g/cm³
Solubility Soluble in hot water, dimethyl sulfoxide, alcohol and benzene.
Melting Point 231-233 °C(lit.)
Formula C₁₀H₁₆N₂O₃S
Boiling Point 573.6 °C at 760 mmHg
Molecular Weight 244.315
Flash Point 300.7 °C
Transport Information
Appearance white powder
Safety 24/25
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 1H-Thieno[3,4-d]imidazole-4-pentanoicacid, hexahydro-2-oxo-, (3aS,4S,6aR)-;1H-Thieno[3,4-d]imidazole-4-pentanoicacid, hexahydro-2-oxo-, [3aS-(3aa,4b,6aa)]-;Biotin (8CI);(+)-Biotin;(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid;Biodermatin;Bios II;Coenzyme R;D(+)-Biotin;Factor S;Factor S (vitamin);Lutavit H2;Meribin;NSC 63865;Rovimix H 2;Vitamin B7;Vitamin H;cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid;Biotin;
PSA 103.73000
LogP 1.45440

Synthetic route

: (2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

: 616-38-6
carbonic acid dimethyl ester

: 58-85-5
biotin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; tin(IV) chloride at 150℃; under 300.03 Torr; for 3.5h; Temperature; Pressure; Reagent/catalyst; Autoclave;	97.5%

: 28092-52-6
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

: 10387-40-3
potassium thioacetate

: 58-85-5
biotin

Conditions

Conditions	Yield
In water at 0 - 60℃; Temperature;	97%

: 5-((3aR,6S,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid

: 58-85-5
biotin

Conditions

Conditions	Yield
With hydrogenchloride; sodium dithionite; water; sodium hydroxide In water at 55 - 90℃; for 0.5h; Reagent/catalyst;	95.8%

: 33607-60-2
(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With boron tribromide In dichloromethane at -5 - 50℃; for 1.16667h; Inert atmosphere; Stage #2: With hydrogenchloride In water Temperature; Solvent;	95%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With water; hydrogen bromide In xylene for 20h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12; Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;	92%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid With water; hydrogen bromide In xylene for 20h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12; Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;	92%

: 31099-31-7
(3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: (3aS,4S,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylpentane nitrile With water; hydrogen bromide In xylene for 20h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12; Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;	95%
With water; hydrogen bromide for 10h; Reflux; Inert atmosphere;	80%
Multi-step reaction with 2 steps 1: aq. HBr / toluene / 40 h / Heating 2: 22 g / aq. NaOH / toluene; methoxybenzene / 6 h / 30 °C View Scheme

: 5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

: 503-38-8
trichloromethyl chloroformate

: 58-85-5
biotin

Conditions

Conditions	Yield
With sodium hydroxide at 20℃; for 10h; pH=9-11;	93%

: 32315-10-9
bis(trichloromethyl) carbonate

: 5-[(2S,3S,4R)-3,4-diaminotetrahydrothiophen-2-yl]pentanoic acid hydrobromide

: 58-85-5
biotin

Conditions

Conditions	Yield
With potassium hydroxide at 20℃; for 10h; pH=9-11; Reagent/catalyst;	92%

: (2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

: 105-58-8
Diethyl carbonate

: 58-85-5
biotin

Conditions

Conditions	Yield
With methanetrisulfonic acid at 170℃; under 3000.3 - 4500.45 Torr; Reagent/catalyst; Pressure; Temperature; Autoclave;	91.67%

: 292151-19-0
(3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester With water; hydrogen bromide In xylene for 20h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12; Stage #3: With hydrogenchloride; bis(trichloromethyl) carbonate; pyrographite Product distribution / selectivity; more than 3 stages;	90%
With sulfuric acid; water; acetic acid at 20 - 80℃;	82%
With methanesulfonic acid In 1,3,5-trimethyl-benzene	74%
Stage #1: (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene)pentanoic acid ethyl ester With hydrogen bromide for 48h; Substitution; Heating; Stage #2: With sodium hydroxide; chloroformic acid ethyl ester Substitution; Stage #3: With hydrogenchloride Hydrolysis;

: 179532-60-6
benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate With water; hydrogen bromide In xylene for 24h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12; Stage #3: With hydrogenchloride; trichloromethyl chloroformate; pyrographite Product distribution / selectivity; more than 3 stages;	90%
Stage #1: benzyl (3aS,4S,6aR)-5-(1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)pentanoate With water; hydrogen bromide In xylene for 20h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=12; Stage #3: With hydrogenchloride; trichloromethyl chloroformate; pyrographite Product distribution / selectivity; more than 3 stages;	90%

: C19H24N2O3S

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: C19H24N2O3S With palladium on activated charcoal; hydrogen In ethanol at 80 - 85℃; under 11400.8 - 15201 Torr; for 15h; Stage #2: With sodium hydroxide In water at 25 - 30℃; for 5h; Solvent;	86.9%

: 83541-80-4
<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

: 58-85-5
biotin

Conditions

Conditions	Yield
With hydrogen bromide	85%
With hydrogen bromide	85%

: 151526-81-7
<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

: 58-85-5
biotin

Conditions

Conditions	Yield
With hydrogen bromide for 2h; Heating;	85%
With hydrogen bromide for 2h; Heating;	85%
Multi-step reaction with 2 steps 1.1: water; NaOH / methanol / 3 h / 40 °C 2.1: MeSO3H / xylene / 3 h / 135 °C 2.2: 3.06 g / water / 1 h / 10 °C View Scheme

: 324012-42-2
(3aS,6aR)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one-4-ylidenepentanoic acid

: 58-85-5
biotin

Conditions

Conditions	Yield
With formic acid; methanesulfonic acid; palladium on activated charcoal for 15h; Catalytic hydrogenation; Debenzylation; Heating;	85%
Multi-step reaction with 2 steps 1: H2 / 10percent Pd/C / propan-2-ol / 18 h / 50 °C / 7500.6 Torr 2: 48percent HBr / 2 h / 100 °C View Scheme

ethyl 5-iodopentanoate: ethyl 5-iodopentanoate

: 28092-52-6
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: ethyl 5-iodopentanoate With bromine; zinc In tetrahydrofuran; toluene at 40℃; for 1h; Stage #2: (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione With palladium 10% on activated carbon In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 28 - 40℃; for 5h; Further stages;	85%

(1-naphthyl)CH2CONH(CH2)2OPO2O-5\-d(GCGAGAAGTTAAGACCTATGCTCGC)-3\-O(CH2)3S-(4-succinimide-1)-(CH2)2O-(p-C6H4)COCH2(biotinate): (1-naphthyl)CH2CONH(CH2)2OPO2O-5\-d(GCGAGAAGTTAAGACCTATGCTCGC)-3\-O(CH2)3S-(4-succinimide-1)-(CH2)2O-(p-C6H4)COCH2(biotinate)

: 58-85-5
biotin

Conditions

Conditions	Yield
With 5'-d(CATAGGTCTTAACTT)-3'; sodium cacodylate In water; isopropyl alcohol at 20℃; pH=7.0; UV-irradiation;	84%

N,N'-p-methoxybenzylbiotin: 1245507-48-5
N,N'-p-methoxybenzylbiotin

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: N,N'-p-methoxybenzylbiotin With hydrogen bromide In toluene for 36h; Reflux; Stage #2: With bis(trichloromethyl) carbonate; methoxybenzene In water for 2h; pH=10;	83%

: 32315-10-9
bis(trichloromethyl) carbonate

: (2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid

: 58-85-5
biotin

Conditions

Conditions	Yield
With sodium hydroxide In water; toluene at -10 - -5℃;	82.38%

: 58-85-5
biotin

Conditions

Conditions	Yield
Stage #1: N,N'-dibenzylbiotin methyl ester With hydrogen bromide for 5h; Heating; Stage #2: With sulfuric acid In methanol for 2h; Heating;	78%
With hydrogen bromide for 5h; Heating;	0.041 g

: 75-44-5
phosgene

: (2S,3S,4R-3,4-diaminotetrahydrothiophen-2-yl)-pentanoate sodium

: 58-85-5
biotin

Conditions

Conditions	Yield
With sodium hydroxide In water; 1,2-dichloro-ethane at 70 - 80℃; for 4h; pH=10 - 12;	75.8%

: 30964-00-2
hept-6-ynoic acid

amine-biotin: amine-biotin

: 543-27-1
isobutyl chloroformate

A alk-biotin: alk-biotin

B: 58-85-5
biotin

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane; N,N-dimethyl-formamide	A n/a B 62%

...Expand

: 75-44-5
phosgene

: 22342-46-7
(2S,3S,4R)-cis-5-(3,4-diaminotetrahydro-2-thienyl)valeric acid

: 58-85-5
biotin

: 58-85-5, 4375-00-2, 4443-68-9, 5652-41-5, 15720-24-8, 21788-37-4, 22377-59-9, 57378-70-8, 58073-87-3, 68225-55-8
(+/-)-biotin

: 58-85-5
biotin

Conditions

Conditions	Yield
With MANDELIC ACID
With (9S)-9-hydroxy-6'-methoxy-1-methyl-cinchonanium hydroxide
With L-arginine

: 76335-62-1
5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid

: 58-85-5
biotin

Conditions

Conditions	Yield
With ammonia; sodium; xylene
Stage #1: 5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid With methanesulfonic acid In xylene at 135℃; for 3h; Stage #2: With water at 10℃; for 1h; Further stages.;	3.06 g
With ammonia; sodium; xylene

: 75-44-5
phosgene

: 64820-06-0
5-[3,4-bis-(2,2,2-trifluoro-acetylamino)-2,5-dihydro-thiophen-2-yl]-pentanoic acid methyl ester

: 58-85-5
biotin

Conditions

Conditions	Yield
(i) H2, Pd/C, (ii) K2CO3, H2O, (iii) /BRN= 1098367/; Multistep reaction;

: 57671-79-1
[3-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-propyl]-malonic acid

: 58-85-5
biotin

Conditions

Conditions	Yield
With sodium hydroxide at 180℃; for 0.5h;

: 66244-06-2
5-((3aS)-1,3-diacetyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester

: 58-85-5
biotin

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water

: Sodium; 5-((3aR,6S,6aS)-1-benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoate

: 58-85-5
biotin

Conditions

Conditions	Yield
With hydrogen bromide for 2h; Heating;

: 67-56-1
methanol

: 58-85-5
biotin

biotin methyl ester: biotin methyl ester

Conditions

Conditions	Yield
With hydrogenchloride for 15h;	100%
With sulfuric acid	100%
Stage #1: methanol With acetyl chloride at 0℃; for 0.166667h; Stage #2: biotin for 1h; Reflux;	100%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 58-85-5
biotin

: 35013-72-0
biotin N-Hydroxysuccinimide ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	98%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	95%

: 64-17-5
ethanol

: 58-85-5
biotin

: 87573-52-2
5-[(3aS,4S,6aR)-2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl]-pentanoic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid	100%
With sulfuric acid at 20℃;	97%
With hydrogenchloride at 0 - 20℃; for 24h;	91%

: 106590-42-5
methyl 10-aminodecanoate hydrochloride

: 58-85-5
biotin

: 10-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-decanoic acid methyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	100%

: 5680-79-5
glycine ethyl ester hydrochloride

: 58-85-5
biotin

: [5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-acetic acid methyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	100%

: 153086-78-3
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

: 58-85-5
biotin

: 175885-18-4
tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 17.5h; Inert atmosphere;	100%
Stage #1: biotin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate In dichloromethane at 20℃; for 16h;	96%

: 929537-66-6
C2HF3O2*C6H14N4O2

: 58-85-5
biotin

: 945633-30-7
N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions

Conditions	Yield
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	100%

: C8H17NO5

: 58-85-5
biotin

: 1123762-87-7
C19H33N3O7S

Conditions

Conditions	Yield
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide	100%

: 1278996-71-6
1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-amine

: 58-85-5
biotin

: 1278996-72-7
1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-biotinylamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	100%

N,N-dimethylethylenediamine: N,N-dimethylethylenediamine

: 58-85-5
biotin

: 1338832-53-3
2-N-biotinyl-N,N-dimethylethan-1,2-diamine

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 24h;	100%

: 58-85-5
biotin

C41H56N4O7S: C41H56N4O7S

Conditions

Conditions	Yield
Stage #1: biotin With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 0.5h; Inert atmosphere; Stage #2: 3-{2-[2-(3-{[Bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-propoxy)-ethoxy]-ethoxy}-propylamine With triethylamine In N,N-dimethyl-formamide Inert atmosphere;	100%

: N-(4-(4-(4-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide

: 58-85-5
biotin

: N-(4-(2,6-dimethyl-4-(4-((13-oxo-17-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-3,6,9-trioxa-12-azaheptadecyl)oxy)piperidin-1-yl)phenyl)thiazol-2-yl)isonicotinamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;	100%

: N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

: 58-85-5
biotin

: N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide	100%

: 2524-49-4
3-butene-1-amine

: 58-85-5
biotin

: C14H23N3O2S

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;	100%

: N-(3-aminopropyl)-N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxybenzenesulfonamide hydrochloride

: 58-85-5
biotin

: N-(3-((N-(4-chloro-2,5-dimethoxyphenyl)-4-ethoxyphenyl)sulfonamido)propyl)-5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide	100%

: 124-09-4
1,6-Hexanediamine

: 58-85-5
biotin

: 65953-56-2
N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide

Conditions

Conditions	Yield
Stage #1: biotin With di(succinimido) carbonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere; Stage #2: 1,6-Hexanediamine In N,N-dimethyl-formamide Inert atmosphere;	99%

: 1071926-11-8
C29H37N5O4

: 58-85-5
biotin

: 1071926-14-1
C39H51N7O6S

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	99%

: 8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-9-(3-isopropylamino-propyl)adenine

: 58-85-5
biotin

: 1418215-37-8
C28H35IN8O4S2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication; Inert atmosphere;	99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication;	99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 9h; Sonication;	99%

: 107-15-3
ethylenediamine

: 58-85-5
biotin

: N-(2-aminoethyl)-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide

Conditions

Conditions	Yield
Stage #1: biotin With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 48 - 63℃; for 0.583333 - 0.666667h; Stage #2: ethylenediamine In N,N-dimethyl-formamide for 72h;	99%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 58-85-5
biotin

: 120550-35-8
biotin pentafluorophenyl ester

Conditions

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide 0-5 deg C, 2.5 h; room temperature, 16 h;	98%
With pyridine; dicyclohexyl-carbodiimide at 20 - 50℃;	95%
With pyridine; 2`,3`-dideoxycytidine at 20℃; for 24h;	93%

: 111-87-5
octanol

: 58-85-5
biotin

: biotin octan-1-ol ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Heating;	98%

: 86520-52-7
2-[2-(2-azidoethoxy)ethoxy]ethanol

: 58-85-5
biotin

: 1085938-08-4
C16H27N5O5S

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere;	65%

: 75-36-5
acetyl chloride

: 58-85-5
biotin

: 608-16-2
biotin methyl ester

Conditions

Conditions	Yield
Stage #1: acetyl chloride In methanol at 0℃; for 0.25h; Stage #2: biotin In methanol at 20℃; for 0.5h;	98%

: 35661-39-3
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

: 35737-15-6
Fmoc-Trp-OH

: 105047-45-8
Fmoc-Lys-OH

: 86123-10-6
Fmoc-D-Phe-OH

: 116611-64-4
(9-fluorenylmethoxycarbonyl)-L-histidine

: 58-85-5
biotin

: C56H70N14O8S

Conditions

Conditions	Yield
Stage #1: Fmoc-Lys-OH With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 4h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h; Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Trp-OH; Fmoc-D-Phe-OH; (9-fluorenylmethoxycarbonyl)-L-histidine; biotin Further stages;	98%

...Expand

: 929521-54-0
N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline

: 58-85-5
biotin

: C22H32N6O8S

Conditions

Conditions	Yield
Stage #1: biotin With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide Stage #2: N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2,4-dinitroaniline In N,N-dimethyl-formamide for 0.166667h;	98%

: 14860-64-1
4-azidoaniline

: 58-85-5
biotin

: N-(4-azidophenyl)biotinamide

Conditions

Conditions	Yield
Stage #1: biotin With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: 4-azidoaniline In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	98%

: 59483-84-0
bis(pentafluorophenyl)carbonate

: 58-85-5
biotin

: 120550-35-8
biotin pentafluorophenyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine In N,N-dimethyl-formamide for 2h;	97%

: 58-85-5
biotin

: 23015-53-4
5-((3aS,4S,6aR)-5-oxido-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid

Conditions

Conditions	Yield
With sodium peroxoborate tetrahydrate; acetic acid at 20℃; for 1.33333h;	97%
With dihydrogen peroxide In acetic acid for 12h; Ambient temperature;

: 136587-00-3
di-tert-butyl 4-<2-(tert-butoxycarbonyl)ethyl>-4-nitroheptanedicarboxylate

: 58-85-5
biotin

: 353737-53-8
Biotinamidotris[2-(tert-butoxycarbonyl)ethyl]methane

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 13h;	97%

D-Biotin Consensus Reports

Reported in EPA TSCA Inventory.

D-Biotin Specification

1. Introduction of D-Biotin

D-Biotin, with the IUPAC Name of 5-[(3aR,6S,6aS)-2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic acid, is one kind of white powder. And this chemical belongs to the Product Category which include cyclic compounds; Miscellaneous Natural Products; Vitamins; Nutritional Supplements; Vitamins and derivatives; Biotin Derivatives; Intermediates & Fine Chemicals; Vitamin Ingredients.

In addition, D-Biotin could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials, light. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, nitrogen.

2. Properties of D-Biotin

D-Biotin has the following datas: (1)Melting point: 231-233 °C; (2)Index of Refraction: 1.544; (3)Density: 1.267 g/cm3; (4)Flash Point: 300.7 °C; (5)Enthalpy of Vaporization: 93.93 kJ/mol; (6)Boiling Point: 573.6 °C at 760 mmHg; (7)Vapour Pressure: 1.19E-14 mmHg at 25 °C.

3. Structure Descriptors of D-Biotin

You could convert the following datas into the molecular structure:
InChI: InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
InChIKey: InChIKey=YBJHBAHKTGYVGT-ZKWXMUAHSA-N
Smiles: N1[C@@H]2[C@@H](NC1=O)CS[C@@H]2CCCCC(O)=O

4. Safety Information of D-Biotin

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x and SO_x.
Hazard Codes: Harmful Xn
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

When on the skin: should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. There is no specific treatment is necessary since this material is not likely to be hazardous by inhalation. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.

5. Use and Preparation of D-Biotin

D-Biotin is nutritional supplement, and is used for animal nutrition in premixes, compound feeds, milk replacers and liquid diets.

Product Name

D-Biotin

Synthetic route

D-Biotin Consensus Reports

D-Biotin Specification

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