Hexadecanedioic acid supplier

Name
Hexadecanedioic acid
EINECS 208-013-5
CAS No. 505-54-4
Article Data43
CAS DataBase
Density 1.016 g/cm³
Solubility 5.098mg/L at 20℃
Melting Point 120-123 °C(lit.)
Formula C₁₆H₃₀O₄
Boiling Point 457.5 °C at 760 mmHg
Molecular Weight 286.412
Flash Point 244.6 °C
Transport Information
Appearance white powder
Safety 24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms 1,14-Tetradecanedicarboxylicacid;1,16-Hexadecanedioic acid;NSC 15164;Thapsic acid;n-Tetradecane-w,w'-dicarboxylic acid;
PSA 74.60000
LogP 4.61700

Synthetic route

: 81393-29-5
C24H38O8

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With hydrogenchloride In water Heating;	95%

: 121626-90-2
hexadec-8t-enedioic acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With methanol; nickel Hydrogenation;
With acetic acid; platinum Hydrogenation;

: 3344-70-5
1,12-dibromododecane

: 996-82-7
sodium diethylmalonate

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
Durch Verseifen und Erhitzen der erhaltenen Tetracarbonsaeure;

: 506-13-8
16-hydroxyhexadecanoic acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid
With chromium(VI) oxide
With chromium(VI) oxide; sulfuric acid In acetone

: 89790-15-8
hexadecanediamide

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 408311-05-7
5,12-dioxo-hexadecanedioic acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol
With hydrogenchloride; amalgamated zinc; acetic acid

: 109155-87-5
7-semicarbazono-hexadecanedioic acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol

: 2550-52-9
cyclohexadecanone

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With chromium(VI) oxide; acetic acid

: 5,12-dioxo-hexadecanedioic acid bis-methylamide

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With sodium; hydrazine hydrate; ethylene glycol

: 544-76-3
Hexadecane

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
(microbiological transformation);

: 1593-55-1
azelaic acid monoethyl ester

: 30993-88-5
9-acetoxy nonanoic acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
(i) (electrochemical oxidation), aq. K2CO3, (ii) KOH, EtOH; Multistep reaction;

: 65119-97-3
heptadec-16-enoic acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With potassium permanganate In acetone

: 19102-90-0
dimethyl hexadecanedioate

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
(saponification);

: 7735-42-4
1,16-hexadecanediol

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With potassium permanganate In water; acetone at 70℃;

: 3974-28-5
5-Oxohexadecanedioic Acid

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
(i) NaOH, N2H4*H2O, (ii) (heating); Multistep reaction;

: 93158-51-1
6-Oxo-hexadecan-disaeure

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol

: 102376-23-8
4-Oxo-tetradecan-dicarbonsaeure-(1,14)-diethylester

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
(i) N2H4*H2O, HOCH2CH2OCH2CH2OH, (ii) KOH, (thermolysis); Multistep reaction;

: 3839-45-0
17-Phenyl-stearinsaeure

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With chromium(VI) oxide In acetic acid at 100℃;

: 17204-92-1
4-Oxo-hexadecandisaeure

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
(i) KOH, N(CH2CH2OH)3, (ii) N2H4*H2O, (iii) KOH; Multistep reaction;

: 57-57-8
β-Propiolactone

: 23708-54-5
1,10-Decandiylbis(magnesiumbromid)

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at 0℃; for 3h;

: 88739-44-0
1-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl-hydroperoxide

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With sulfuric acid; water; iron(II) sulfate 1.) 0 deg C, methanol 2.) RT; Yield given. Multistep reaction;

: 2,3,19-Trioxabicyclo<14.2.1>nonadecane

A: 505-54-4
thapsic acid

B: 69275-06-5
15-formylpentadecanoic acid

Conditions

Conditions	Yield
In benzene-d6 at 80℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 623-11-0
1-methyl-4-nitrosobenzene

: 857979-06-7
6-[5-(5-carboxy-[2]thienylmethyl)-[2]thienyl]-hexanoic acid

nickel-aluminium-alloy: nickel-aluminium-alloy

: 505-54-4
thapsic acid

...Expand

: 4653-11-6
2-thiophenebutyric acid

aqueous sodium carbonate-solution: aqueous sodium carbonate-solution

Raney nickel: Raney nickel

A: 124-07-2
Octanoic acid

B: 505-54-4
thapsic acid

...Expand

7-oxo-tetradecane-dicarboxylic acid-(1.14): 7-oxo-tetradecane-dicarboxylic acid-(1.14)

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With hydrogenchloride; amalgamated zinc unter Durchleiten von Chlorwasserstoff;

: 19812-64-7
1,14-tetradecanediol

carbon monoxide: carbon monoxide

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With iodine; tetracarbonyl nickel at 260℃; under 147102 Torr;

zibetan: zibetan

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
With permanganate(VII) ion; benzene

: 67788-03-8
(E)-tert-butyl (cyclooct-1-en-1-yloxy)dimethylsilane

: 505-54-4
thapsic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O2 / trifluoroacetic acid 2: 1.)FeSO4 2.) H2O, H2SO4 / 1.) 0 deg C, methanol 2.) RT View Scheme

: 505-54-4
thapsic acid

: 7735-42-4
1,16-hexadecanediol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux;	96%
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Reduction; Heating;	92%
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;	84%

: 505-54-4
thapsic acid

: 34959-19-8
1,16-hexadecanedioyl dichloride

Conditions

Conditions	Yield
With thionyl chloride In benzene for 2h; Heating;	95%
With thionyl chloride for 3h; Heating;
With thionyl chloride for 1h; Heating;

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

: 505-54-4
thapsic acid

: 191091-30-2
hexadecanedioic acid bis-(2,5-dioxopyrrolidin-1-yl)ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;	95%

: 505-54-4
thapsic acid

: 100-51-6
benzyl alcohol

: dibenzyl hexadecanedioate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 120℃; for 24h;	95%
With toluene-4-sulfonic acid In toluene for 8h; Heating / reflux;

: 505-54-4
thapsic acid

: 1146622-60-7
N1-(tert-butoxycarbonyl)-N2-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine

: 1356946-87-6
N1,N16-bis{(tert-butoxycarbonylamino)[3-(1-trityl-1H-imidazol-4-yl)propylamino]methylene}hexadecanediamide

Conditions

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: N1-(tert-butoxycarbonyl)-N2-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine In dichloromethane at 20℃; Inert atmosphere;	88%

: 505-54-4
thapsic acid

: 56-81-5
glycerol

: hexadecandioic acid bis(2,3-dihydroxypropyl)ester

Conditions

Conditions	Yield
With mesoporous silica HMS2-SO3H at 110℃; for 6h; Product distribution; Further Variations:; Reagents; reaction times;	86%

: 505-54-4
thapsic acid

: 302-27-2
acotinine

: C48H73NO13

Conditions

Conditions	Yield
With 2,3,5-trimethyl-pyridine In tetrahydrofuran at 70℃; for 5h;	85.5%

: 505-54-4
thapsic acid

: 104-15-4
toluene-4-sulfonic acid

: 1,14-tetradecyldiammonium ditosylate

Conditions

Conditions	Yield
Stage #1: thapsic acid With sodium azide; sulfuric acid In chloroform at 50℃; for 2h; Schmidt Reaction; Stage #2: toluene-4-sulfonic acid	73%

: 505-54-4
thapsic acid

: 11-amino-N-(strychnin-2-yl)undecanoic acid amide

: N1,N16-Bis[N-(strychnine-2-yl)undecanoic Acid Amide-11-yl]hexadecanediamide

Conditions

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: 11-amino-N-(strychnin-2-yl)undecanoic acid amide In dichloromethane at 20℃; for 14h; Inert atmosphere; Cooling with ice;	71%

: 67-56-1
methanol

: 505-54-4
thapsic acid

: 19102-90-0
dimethyl hexadecanedioate

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 4h;	69%
With thionyl chloride at 20℃; for 6h;

: 64-17-5
ethanol

: 505-54-4
thapsic acid

A: 15786-31-9
diethyl hexadecanedioate

B: 18017-66-8
hexadecanedioic acid monoethyl ester

Conditions

Conditions	Yield
With sulfuric acid In cyclohexane for 48h;	A n/a B 68%

...Expand

: 505-54-4
thapsic acid

: 70-11-1
α-bromoacetophenone

: 443770-14-7
hexadecanedioic acid mono-(2-oxo-2-phenyl-ethyl) ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 24h;	65%

: 108-05-4
vinyl acetate

: 505-54-4
thapsic acid

: 160907-11-9
divinyl hexadecanedioate

Conditions

Conditions	Yield
With sulfuric acid; mercury(II) diacetate for 4h; Reflux; Inert atmosphere;	64%

: 3590-93-0, 85440-15-9, 123287-54-7, 123287-57-0
4'-demethyl-4-deoxypodophyllotoxin

: 505-54-4
thapsic acid

: Hexadecanedioic acid mono-[2,6-dimethoxy-4-((5R,5aR,8aR)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl] ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	63%

: 505-54-4
thapsic acid

: 89965-56-0
<3-<<4-(carboxyamino)butyl>amino>propyl>carbamic acid, dibenzyl ester

: 177334-75-7
15-[(4-Benzyloxycarbonylamino-butyl)-(3-benzyloxycarbonylamino-propyl)-carbamoyl]-pentadecanoic acid

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	62%

: 505-54-4
thapsic acid

: 1151467-62-7
tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]thiazol-2-yl-carbamate

: 1356946-78-5
N1,N16-bis((tert-butoxycarbonylamino){3-[2-(tert-butoxycarbonyl)aminothiazol-5-yl]propylamino}methylene)hexadecanediamide

Conditions

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]thiazol-2-yl-carbamate In dichloromethane at 20℃; Inert atmosphere;	62%

: 505-54-4
thapsic acid

: 443-48-1
metronidazole

: 848046-35-5
16-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)-16-oxohexadecanoic acid

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h;	60%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 40℃; for 24h;	57.4%
Stage #1: thapsic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h; Stage #2: metronidazole With dmap In tetrahydrofuran	37.2%
Stage #1: thapsic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h; Stage #2: metronidazole With dmap In tetrahydrofuran	37.2%

: 505-54-4
thapsic acid

: 213403-58-8
N-trityl-N,N'-bis-[3-(trityl-amino)-propyl]-butane-1,4-diamine

: C150H162N8O2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 24h;	57%

: 505-54-4
thapsic acid

: 100-39-0
benzyl bromide

: 146004-98-0
16-(benzyloxy)-16-oxohexadecanoic acid

Conditions

Conditions	Yield
With sodium carbonate In 2-methyltetrahydrofuran; water at 75℃; for 22h;	55.6%
With tetrabutylammomium bromide; potassium hydroxide In methanol Inert atmosphere;	42%

: 505-54-4
thapsic acid

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	55%

tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]-4-methylthiazol-2-yl-carbamate: tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]-4-methylthiazol-2-yl-carbamate

: 1356946-70-7
N1,N16-bis((tert-butoxycarbonylamino){3-[2-(tert-butoxycarbonyl)amino-4-methylthiazol-5-yl]propylamino}methylene)hexadecanediamide

Conditions

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]-4-methylthiazol-2-yl-carbamate In dichloromethane at 20℃; Inert atmosphere;	54%

: 505-54-4
thapsic acid

: 69655-05-6
Dideoxyinosine

: 879015-25-5
2',3'-dideoxy-5'-hydrogen hexadecanedioate inosine

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	50.5%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	50.5%

: 505-54-4
thapsic acid

: 110224-49-2
template CS diol

: 124461-68-3
C67H74O4

Conditions

Conditions	Yield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In chloroform for 14h; Heating;	50%

: 505-54-4
thapsic acid

: 100-44-7
benzyl chloride

: 146004-98-0
16-(benzyloxy)-16-oxohexadecanoic acid

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 80℃; for 40h;	50%

: 505-54-4
thapsic acid

: 36805-97-7
N,N-dimethylformamide di-tert-butyl acetal

: 843666-27-3
hexadecanedioic acid mono-tert-butyl ester

Conditions

Conditions	Yield
In toluene Reflux;	49%
In toluene Reflux;	47.6%
Stage #1: thapsic acid; N,N-dimethylformamide di-tert-butyl acetal In toluene at 50℃; Stage #2: With ethyl acetate In dichloromethane for 0.25h;	33%

: 505-54-4
thapsic acid

: 10597-60-1
hydroxytyrosol

: bis(3,4-dihydroxyphenethyl) hexadecanedioate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 75℃;	48%

: 505-54-4
thapsic acid

: 5391-18-4, 25320-93-8, 39824-09-4, 95531-15-0, 143289-25-2, 146453-36-3, 148347-27-7
butyl-α-D-glucopyranoside

: butyl 6-O-hexadecanedioyl-α-D-glucopyranoside

Conditions

Conditions	Yield
pig pancreatic lipase In acetone at 45℃; for 72h;	47%

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

: 505-54-4
thapsic acid

: ω-carboxypentanedecanoic acid monosuccinimidyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane; ethyl acetate at 20℃; for 12h;	45%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h;	41%

: 7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

: 505-54-4
thapsic acid

: 1350462-77-9
C54H66F2N6O12

Conditions

Conditions	Yield
Stage #1: thapsic acid With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: 7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 50℃; for 72h;	41%

Hexadecanedioic acid Specification

The Hexadecanedioic acid, with the CAS registry number 121570-10-3 and EINECS registry number 208-013-5, is a kind of white power, and belongs to the following product categories: alpha,omega-Alkanedicarboxylic Acids; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes. And the molecular formula of the chemical is C₁₆H₃₀O₄.

The characteristics of this chemical are as followings: (1)ACD/LogP: 5.05; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.46; (4)ACD/LogD (pH 7.4): 0.43; (5)ACD/BCF (pH 5.5): 103.72; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 340.48; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 15; (12)Polar Surface Area: 52.6 Å²; (13)Index of Refraction: 1.474; (14)Molar Refractivity: 79.3 cm³; (15)Molar Volume: 281.8 cm³; (16)Polarizability: 31.43×10^-24cm³; (17)Surface Tension: 40.7 dyne/cm; (18)Density: 1.016 g/cm³; (19)Flash Point: 244.6 °C; (20)Enthalpy of Vaporization: 78.65 kJ/mol; (21)Boiling Point: 457.5 °C at 760 mmHg; (22)Vapour Pressure: 1.22E-09 mmHg at 25°C.

Uses of Hexadecanedioic acid: It can be used to produce hexadecanedioyl chloride. This reaction will need reagent SOCl₂, and the menstruum benzene. The reaction time is 2 hours with heating, and the yield is about 95%.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better avoid contacting with skin and eyes .

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(O)CCCCCCCCCCCCCCC(=O)O
(2)InChI: InChI=1/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)
(3)InChIKey: QQHJDPROMQRDLA-UHFFFAOYAF

Product Name

Hexadecanedioic acid

Synthetic route

Hexadecanedioic acid Specification

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