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58-85-5

Basic Information
CAS No.: 58-85-5
Name: D-Biotin
Article Data: 122
Cas Database
Molecular Structure:
Molecular Structure of 58-85-5 (D-Biotin)
Formula: C10H16N2O3S
Molecular Weight: 244.315
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;
EINECS: 200-399-3
Density: 1.267 g/cm3
Melting Point: 231-233 °C(lit.)
Boiling Point: 573.6 °C at 760 mmHg
Flash Point: 300.7 °C
Solubility: Soluble in hot water, dimethyl sulfoxide, alcohol and benzene.
Appearance: white powder
Hazard Symbols: Xn
Risk Codes: 20/21/22-36/37/38
Safety: 24/25
Transport Information: N/A
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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-benzene74%
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
ConditionsYield
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%
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Consensus Reports

Reported in EPA TSCA Inventory.

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 NOx and SOx.
Hazard Codes: HarmfulXn
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.

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