532-40-1

Basic information

• Product Name: THIAMINE MONOPHOSPHATE CHLORIDE
• Synonyms: THIAMINE MONOPHOSPHATE CHLORIDE;thiaminemonophosphate;LABOTEST-BB LT00847627;monophosphothiamine;Phosphothiaminum;Thiazolium, 3-(4-amino-2-methyl-5-pyrimidinyl)methyl-4-methyl-5-2-(phosphonooxy)ethyl-, chloride;3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-thiazolium chloride;Thiamin monophosphate chloride
• CAS NO: 532-40-1
• Molecular Formula: C₁₂H₁₈N₄O₄PS*Cl
• Molecular Weight: 380.79
• EINECS: 208-536-9
• Mol File: 532-40-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: ~200°
• Appearance: /
• Density: 1.53[at 20℃]
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• Water Solubility: 176g/L at 20℃
• Stability: Hygroscopic
• CAS DataBase Reference: THIAMINE MONOPHOSPHATE CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: THIAMINE MONOPHOSPHATE CHLORIDE(532-40-1)
• EPA Substance Registry System: THIAMINE MONOPHOSPHATE CHLORIDE(532-40-1)

Safety Data

• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 532-40-1(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

Vitamin B1 Monophosphate Chloride is a precursor of thiamine pyrophosphate (T344070), a thiamine (T344185) derivative produced by enzyme thiamine pyrophosphatase. Thiamine pyrophosphate is a cofactor used to catalyze various biochemical reactions.

Flammability and Explosibility

Notclassified

Purification Methods

Purify it by recrystallisation from aqueous HCl, EtOH slightly acidified with HCl, EtOH/Me2CO, H2O, or H2O/EtOH/Et2O. Dissolve it in a small volume of H2O and mix it with EtOH/Me2CO (1:1) to give the HCl.H2O as crystals. Filter it off, wash it with Et2O and dry it in a vacuum. The chloride hydrochloride, m 215-217o(dec) is obtained when it is crystallised from aqueous HCl. [Wenz et al. Justus Liebigs Ann Chem 618 2280 1958, Viscontini et al. Helv Chim Acta 34 1388 1951, Leichssenring & Schmidt Chem Ber 95 767 1962, McCormick & Wright Methods Enzymol 18A 141, 147 1970, Beilstein 27 III/IV 1766.]

InChI:InChI=1/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H

Synthetic route

thiamine triphosphate (3475-65-8) → thiamine monophosphate chloride (532-40-1)

Conditions	Yield
With barium dihydroxide

Thiamine hydrochloride (67-03-8) → thiamine monophosphate chloride (532-40-1)

Conditions	Yield
With sodium pyrophosphate; pyrophosphoric acid
Stage #1: Thiamine hydrochloride With sodium pyrophosphate at 120℃; Stage #2: With tributyl-amine In chloroform at 25℃;	862 g

thiamine diphosphate (154-87-0) → thiamine monophosphate chloride (532-40-1)

Conditions	Yield
With sulfuric acid

4-Amino-2-methyl-5-bromomethylpyrimidine dihydrobromide (2908-71-6, 5423-98-3, 31933-50-3) + phosphoric acid mono-[2-(4-methyl-thiazol-5-yl)-ethyl] ester; disodium salt (4066-52-8, 4394-24-5) → thiamine monophosphate chloride (532-40-1)

Conditions	Yield
(i) , (ii) ion exchange resin, Cl-; Multistep reaction;

Thiamine hydrochloride (67-03-8) → thiamine monophosphate chloride (532-40-1) + thiamine diphosphate (154-87-0)

Conditions	Yield
With sodium pyrophosphate at 120℃;

vitamin B1 (59-43-8) → thiamine monophosphate chloride (532-40-1)

Conditions	Yield
With polyphosphoric acid at 100 - 120℃; for 4h; Temperature;

tetra[μ-acetato-bis(methanol)]dirhodium + thiamine monophosphate chloride (532-40-1) → Rh(2+)*2CH3COO(1-)*CH3C4N2H(NH2)CH2NC3SH(CH3)CH2CH2OPO3H=RhC16H23N4O8PS

Conditions	Yield
With NaOH; H2O In water soln. of (Rh2(AcO)4)*2MeOH in hot (80°C) water and thiamin monophosphate chloride in water mixed, pH adusted to 6 with NaOH soln.; soln.allowed to stand for 1 day at room temp., crystn.; crystals filtered off, washed with water and air-dried; elem. anal.;	67%

water (7732-18-5) + thiamine monophosphate chloride (532-40-1) + cadmium(II) chloride (10108-64-2) → C12H18N4O4PS(1+)*0.5CdCl4(2-)*2H2O

Conditions	Yield
In methanol at 20℃; for 168h;	60.3%

thiamine monophosphate chloride (532-40-1) + sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1) → C12H18N4O4PS(1+)*C32H12BF24(1-)

Conditions	Yield
In water; acetonitrile at 0℃; for 24h;	55%

thiamine triphosphate (3475-65-8) + thiamine monophosphate chloride (532-40-1) + thiamine diphosphate (154-87-0) → thiamine monophosphate

Conditions	Yield
In water

water (7732-18-5) + thiamine monophosphate chloride (532-40-1) + mercury dibromide → CH3C4HNH2N2CH2C3HCH3NSCH2CH2OPO3H2(1+)*2Hg(2+)*5Br(1-)*0.5H2O=CH3C4HN2NH2CH2C3HCH3SNCH2CH2OPO3H2Hg2Br5*0.5H2O

Conditions	Yield
In ethanol; water HgBr2 in EtOH was added to soln. of ligand in water, pH 4, allowed to stand at room temp.; elem. anal.;

potassium tetraiodomercurate(II) + thiamine monophosphate chloride (532-40-1) → 2CH3C4HNH2N2CH2C3HCH3NSCH2CH2OPO3H2(1+)*3Hg(2+)*8I(1-)=(CH3C4HN2NH2CH2C3HCH3SNCH2CH2OPO3H2)2Hg3I8

Conditions	Yield
In methanol; water soln. of ligand in water was added to K2HgI4 in MeOH; filtered, dissolved in hot water (55°C), allowed to stand at roomtemp. pH 4; elem. anal.;

potassium tetranitroplatinate(IV) + thiamine monophosphate chloride (532-40-1) → (thiamine)2[Pt(NO2)4]*2H2O

Conditions	Yield
In water pH about 4; crystd. at room temp. for hours;

thiamine monophosphate chloride (532-40-1) → C12H18N4O4PS(1+)*NO3(1-)

Conditions	Yield
With cobalt(II) nitrate hexahydrate In methanol; water at 20℃; for 168h;

thiamine monophosphate chloride (532-40-1) + cucurbit[7]uril → C12H18N4O4PS(1+)*C42H42N28O14

Conditions	Yield
In water at 20℃;

thiamine monophosphate chloride (532-40-1) → C12H18N4O5PS(1-)*Na(1+)

Conditions	Yield
With sodium hydroxide In water at 0 - 5℃; pH=9 - 11; pH-value;

thiamine monophosphate chloride (532-40-1) + m-anisoyl chloride (1711-05-3) → (Z)-S-(2-(N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido)-5-(phosphonooxy)pent-2-en-3-yl)3-methoxybenzothioate

Conditions	Yield
Stage #1: thiamine monophosphate chloride With sodium hydroxide In water at 0 - 5℃; for 1.5h; pH=11 - 12; Stage #2: m-anisoyl chloride In water at 0 - 10℃; for 2h; pH=11 - 12;	11 g
Stage #1: thiamine monophosphate chloride With sodium hydroxide In water at 0 - 5℃; for 1.5h; pH=11-12; Stage #2: m-anisoyl chloride In water at 0 - 10℃; for 2h; pH=11-12;	11 g

Reaxys ID: 33945762 + thiamine monophosphate chloride (532-40-1) → Reaxys ID: 33945761

Reaxys ID: 37389399 + thiamine monophosphate chloride (532-40-1) → Reaxys ID: 37389398

Upstream product

• 67-03-8 Thiamine hydrochloride 
• 154-87-0 thiamine diphosphate 
• 2908-71-6 4-Amino-2-methyl-5-bromomethylpyrimidine dihydrobromide 
• 4066-52-8 phosphoric acid mono-[2-(4-methyl-thiazol-5-yl)-ethyl] ester; disodium salt 
• 59-43-8 vitamin B₁ 
• 3475-65-8 thiamine triphosphate 

Downstream Products

• 22457-89-2 S-[2-[[(4-amino-2-methyl-5 pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propenyl] ester 

Relevant articles and documents

Benfotiamine related substance, preparation method, application and detection method

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