Product Name

  • Name

    Thiamine chloride

  • EINECS 200-425-3
  • CAS No. 59-43-8
  • Article Data18
  • CAS DataBase
  • Density 6 g/cm3
  • Solubility
  • Melting Point 125 °C
  • Formula C12H17ClN4OS
  • Boiling Point
  • Molecular Weight 337.273
  • Flash Point
  • Transport Information
  • Appearance white fine powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 59-43-8 (Thiamine chloride)
  • Hazard Symbols
  • Synonyms VB1;Thiamine(8CI);Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride (9CI);Aneurine;Apatate Drape;Beivon;Bethiamin;Oryzanin;Thiacoat;Thiamin;Thiamine monochloride;Vitamin B1;Vitaneurin;thiamine;3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride;
  • PSA 104.15000
  • LogP -1.80710

Synthetic route

Thiamine hydrochloride
67-03-8

Thiamine hydrochloride

vitamin B1
59-43-8

vitamin B1

Conditions
ConditionsYield
With sodium hydroxide In ethanol100%
3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione
299-35-4

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione

vitamin B1
59-43-8

vitamin B1

Conditions
ConditionsYield
(i) aq. H2O2, (ii) aq. HCl; Multistep reaction;
3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-2-hydroxymethyl-4-methyl-thiazolium; chloride monohydrochloride
22580-38-7

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-2-hydroxymethyl-4-methyl-thiazolium; chloride monohydrochloride

vitamin B1
59-43-8

vitamin B1

Conditions
ConditionsYield
With hydrogenchloride
[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phenyl-methanone
24912-08-1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phenyl-methanone

vitamin B1
59-43-8

vitamin B1

Conditions
ConditionsYield
With hydrogenchloride In ethanol; acetone Ambient temperature;
2-(α-hydroxybenzyl)thiaminium chloride
27350-85-2, 134876-54-3

2-(α-hydroxybenzyl)thiaminium chloride

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

vitamin B1
59-43-8

vitamin B1

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With potassium hydroxide; oxygen In methanol Mechanism; and under aerobic conditions;
...Expand
methanol
67-56-1

methanol

2-(α-hydroxybenzyl)thiaminium chloride
27350-85-2, 134876-54-3

2-(α-hydroxybenzyl)thiaminium chloride

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

vitamin B1
59-43-8

vitamin B1

Conditions
ConditionsYield
With thymoquinone; sodium acetate; acetic acid Rate constant; var. conc. of quinone and buffer; var. quinones;
With oxygen; sodium acetate; acetic acid at 25℃; Mechanism; Rate constant;
...Expand
5-(aminomethyl)-2-methylpyrimidin-4-amine
95-02-3

5-(aminomethyl)-2-methylpyrimidin-4-amine

vitamin B1
59-43-8

vitamin B1

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) aq. NaOH, H2S, EtOH, (ii) /BRN= 126861/, (iii) /BRN= 1854721/
2: aq. HCl / ethanol; acetone / Ambient temperature
View Scheme
vitamin B1
59-43-8

vitamin B1

lithium 4,4,5,5,6,6-hexafluorodihydro-4H-1,3,2-dithiazine 1,1,3,3-tetraoxide

lithium 4,4,5,5,6,6-hexafluorodihydro-4H-1,3,2-dithiazine 1,1,3,3-tetraoxide

C12H17N4OS(1+)*2C3F6NO4S2(1-)*H(1+)

C12H17N4OS(1+)*2C3F6NO4S2(1-)*H(1+)

Conditions
ConditionsYield
With water In water at 20℃;90%
vitamin B1
59-43-8

vitamin B1

bis(trifluoromethane)sulfonimide lithium
90076-65-6

bis(trifluoromethane)sulfonimide lithium

C12H17N4OS(1+)*2C2F6NO4S2(1-)*H(1+)

C12H17N4OS(1+)*2C2F6NO4S2(1-)*H(1+)

Conditions
ConditionsYield
With water at 20℃;89%
vitamin B1
59-43-8

vitamin B1

N4-sulfamoylthiamine

N4-sulfamoylthiamine

Conditions
ConditionsYield
With pyridine; sulfamate de pentachlorophenyle at 100℃; for 2h;86%
vitamin B1
59-43-8

vitamin B1

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

C12H17N4OS(1+)*Cl(1-)*C8Cl2N2O2

C12H17N4OS(1+)*Cl(1-)*C8Cl2N2O2

Conditions
ConditionsYield
In methanol at 25℃;83.3%
vitamin B1
59-43-8

vitamin B1

lithium bis((pentafluoroethyl)sulfonyl)amide

lithium bis((pentafluoroethyl)sulfonyl)amide

C12H17N4OS(1+)*2C4F10NO4S2(1-)*H(1+)

C12H17N4OS(1+)*2C4F10NO4S2(1-)*H(1+)

Conditions
ConditionsYield
With water at 20℃;83%
3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone
87-88-7

3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone

vitamin B1
59-43-8

vitamin B1

C12H17N4OS(1+)*Cl(1-)*C6H2Cl2O4

C12H17N4OS(1+)*Cl(1-)*C6H2Cl2O4

Conditions
ConditionsYield
In methanol at 25℃; for 1h;80.1%
vitamin B1
59-43-8

vitamin B1

thiamin ylide (*1.18 NaCl)
2942-53-2

thiamin ylide (*1.18 NaCl)

Conditions
ConditionsYield
With sodium ethanolate In ethanol at -10 - -5℃; for 0.5h;80%
vitamin B1
59-43-8

vitamin B1

palladium diacetate
3375-31-3

palladium diacetate

C12H16Cl2N4OPdS

C12H16Cl2N4OPdS

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran at 20℃; for 5h; Reflux;80%
3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid
521-15-3

3-(3-oxo-4-androsten-17β-oxycarbonyl)propionic acid

vitamin B1
59-43-8

vitamin B1

3-{4-[3-(10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yloxycarbonyl)propionylamino]-2-methyl-pyrimidin-5-ylmethyl}-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride
1325716-77-5

3-{4-[3-(10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yloxycarbonyl)propionylamino]-2-methyl-pyrimidin-5-ylmethyl}-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; acetonitrile at 20℃; for 48h;73%
vitamin B1
59-43-8

vitamin B1

C12H17IN4OS(2+)*Cl(1-)*I3(1-)

C12H17IN4OS(2+)*Cl(1-)*I3(1-)

Conditions
ConditionsYield
With iodine In methanol at 25℃; for 0.666667h;70%
vitamin B1
59-43-8

vitamin B1

5‐(azidomethyl)‐2‐methylpyrimidin‐4‐amine
63423-50-7

5‐(azidomethyl)‐2‐methylpyrimidin‐4‐amine

Conditions
ConditionsYield
Stage #1: vitamin B1 With sodium azide; sodium sulfite In water at 65℃; for 5h;
Stage #2: With citric acid In water at 20℃; for 0.5h; pH=Ca. 4;
Stage #3: With potassium carbonate In water pH=8;		65%
With sodium azide; sodium sulfite In water at 65℃; for 5h;63%
With sodium azide; sodium sulfite In water at 65℃; for 5h;63%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

vitamin B1
59-43-8

vitamin B1

[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-pyridin-3-yl-methanone
1026039-92-8

[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-pyridin-3-yl-methanone

Conditions
ConditionsYield
With triethylamine In methanol for 1h; Heating;29%
vitamin B1
59-43-8

vitamin B1

aniline
62-53-3

aniline

N-(2-methyl-4-amino-5-pyrimidinyl)methylaniline
1886-29-9

N-(2-methyl-4-amino-5-pyrimidinyl)methylaniline

Conditions
ConditionsYield
With sodium thiosulfate In ethanol; water for 1h; Heating;25%
furfural
98-01-1

furfural

vitamin B1
59-43-8

vitamin B1

A

furil
492-94-4

furil

B

furan-2-yl-[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-methanone
28168-46-9

furan-2-yl-[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-methanone

C

furoin
552-86-3

furoin

Conditions
ConditionsYield
With triethylamine; acrylonitrile In ethanol for 2h;A 3%
B 10%
C 23%
With triethylamine; acrylonitrile In ethanol for 2h; Product distribution; other thiamine derivatives, var. solvents, reaction times and temp.;A 3%
B 10%
C 23%
...Expand
morpholine
110-91-8

morpholine

carbon disulfide
75-15-0

carbon disulfide

vitamin B1
59-43-8

vitamin B1

morpholine-4-carbodithioic acid 4-amino-2-methyl-pyrimidin-5-ylmethyl ester
26608-22-0

morpholine-4-carbodithioic acid 4-amino-2-methyl-pyrimidin-5-ylmethyl ester

...Expand
furfural
98-01-1

furfural

vitamin B1
59-43-8

vitamin B1

furan-2-yl-[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-methanone
28168-46-9

furan-2-yl-[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-methanone

Conditions
ConditionsYield
With triethylamine In methanol for 5h; Heating;
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

methanol
67-56-1

methanol

vitamin B1
59-43-8

vitamin B1

1-[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-3-methoxy-3-phenyl-propan-1-one
28168-52-7

1-[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-3-methoxy-3-phenyl-propan-1-one

Conditions
ConditionsYield
With triethylamine for 5h; Heating;
...Expand
methanol
67-56-1

methanol

di-adamantan-1-yl-tetrasulfane
51171-25-6

di-adamantan-1-yl-tetrasulfane

vitamin B1
59-43-8

vitamin B1

[6a-adamantan-1-yldisulfanyl-3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-methanol
66241-47-2

[6a-adamantan-1-yldisulfanyl-3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-methanol

Conditions
ConditionsYield
(γ-irradiation);
...Expand
methanol
67-56-1

methanol

vitamin B1
59-43-8

vitamin B1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dimethyl ester
17749-80-3

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
(i) Et3N, (ii) diphenyl hydrogen phosphite; Multistep reaction;
phosgene
75-44-5

phosgene

vitamin B1
59-43-8

vitamin B1

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-chlorocarbonyloxy-ethyl)-4-methyl-thiazolium; chloride
96793-20-3

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-chlorocarbonyloxy-ethyl)-4-methyl-thiazolium; chloride

Conditions
ConditionsYield
In acetic acid
methyl phosphite
96-36-6, 868-85-9

methyl phosphite

vitamin B1
59-43-8

vitamin B1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dimethyl ester
17749-80-3

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
(i) Et3N, MeOH, (ii) /BRN= 1697490/; Multistep reaction;
Ethyl isothiocyanate
542-85-8

Ethyl isothiocyanate

vitamin B1
59-43-8

vitamin B1

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-1',3'-diethyl-3a-methyl-tetrahydro-spiro[furo[2,3-d]thiazole-2,4'-imidazolidine]-2',5'-dithione
23972-04-5

3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-1',3'-diethyl-3a-methyl-tetrahydro-spiro[furo[2,3-d]thiazole-2,4'-imidazolidine]-2',5'-dithione

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide
Diethyl phosphonate
762-04-9, 123-22-8

Diethyl phosphonate

vitamin B1
59-43-8

vitamin B1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid diethyl ester
17958-67-7

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
(i) Et3N, EtOH, (ii) /BRN= 1839985/; Multistep reaction;
dipropyl phosphite
54722-86-0

dipropyl phosphite

vitamin B1
59-43-8

vitamin B1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dipropyl ester
21585-60-4

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dipropyl ester

Conditions
ConditionsYield
(i) Et3N, nPrOH, (ii) /BRN= 1840391/; Multistep reaction;
dibutyl hydrogen phosphite
109-47-7

dibutyl hydrogen phosphite

vitamin B1
59-43-8

vitamin B1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibutyl ester
21585-61-5

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibutyl ester

Conditions
ConditionsYield
(i) Et3N, nBuOH, (ii) /BRN= 1840736/; Multistep reaction;
dibutyl hydrogen phosphite
109-47-7

dibutyl hydrogen phosphite

vitamin B1
59-43-8

vitamin B1

A

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibutyl ester
21585-61-5

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibutyl ester

B

[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phosphonic acid dibutyl ester
25714-92-5

[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phosphonic acid dibutyl ester

Conditions
ConditionsYield
(i) Et3N, nBuOH, (ii) /BRN= 1840736/; Multistep reaction;
...Expand
dibenzyl hydrogen phosphite
538-60-3

dibenzyl hydrogen phosphite

vitamin B1
59-43-8

vitamin B1

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibenzyl ester
21585-63-7

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibenzyl ester

Conditions
ConditionsYield
(i) Et3N, MeCN, (ii) /BRN= 2132437/; Multistep reaction;
dibenzyl hydrogen phosphite
538-60-3

dibenzyl hydrogen phosphite

vitamin B1
59-43-8

vitamin B1

A

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibenzyl ester
21585-63-7

[3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phosphonic acid dibenzyl ester

B

[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phosphonic acid dibenzyl ester
21585-64-8

[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phosphonic acid dibenzyl ester

Conditions
ConditionsYield
(i) Et3N, MeCN, (ii) /BRN= 2132437/; Multistep reaction;
...Expand
di-adamantan-1-yl-tetrasulfane
51171-25-6

di-adamantan-1-yl-tetrasulfane

vitamin B1
59-43-8

vitamin B1

5-(6a-adamantan-1-yldisulfanyl-3a-methyl-tetrahydro-furo[2,3-d]thiazol-3-ylmethyl)-2-methyl-pyrimidin-4-ylamine
66241-46-1

5-(6a-adamantan-1-yldisulfanyl-3a-methyl-tetrahydro-furo[2,3-d]thiazol-3-ylmethyl)-2-methyl-pyrimidin-4-ylamine

Conditions
ConditionsYield
(γ-irradiation);

Thiamine chloride Specification

The Thiamine chloride, with the CAS registry number 59-43-8 and EINECS registry number 200-425-3, has the systematic name of 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride. It is also known as vitamin B1, and belongs to the following product categories: Vitamins and Derivatives; Nutritional Supplements; Vitamin Ingredients. And the molecular formula of this chemical is C12H17ClN4OS.

The Thiamine chloride is a colorless compound, and it is stable at acidic pH, but is unstable in alkaline solutions. It is unstable to heat, but stable during frozen storage. It is also unstable when exposed to ultraviolet light and gamma irradiation. Thiamine chloride is soluble in water, methanol, and glycerol, but practically insoluble in acetone, ether, chloroform, and benzene.

The physical properties of Thiamine chloride are as following: (1)#H bond acceptors: 5; (2)#H bond donors: 3; (3)#Freely Rotating Bonds: 5; (4)Polar Surface Area: 70.37 Å2.

Preparation and uses of Thiamine chloride: It can be prepared by acetamidine hydrochloride and dimethoxy-β-α-methoxy propionitrile via a series of condensation, hydrolyzation, neutralization, oxidation and acidification. What's more, it is often used as feed additive. And it palys an important role in the normal activities of the digestive system and nerve conduction.
 
You can still convert the following datas into molecular structure:
(1)SMILES: [Cl-].n1c(c(cnc1C)C[n+]2c(c(sc2)CCO)C)N
(2)InChI: InChI=1/C12H17N4OS.ClH/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);1H/q+1;/p-1
(3)InChIKey: MYVIATVLJGTBFV-REWHXWOFAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo multiple routes 214mg/kg/30W- (214mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 30, Pg. 407, 1995.
mouse LD50 subcutaneous 301mg/kg (301mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957.

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