40137-22-2

Basic information

• Product Name: 3-Methylamino-1,2-propanediol
• Synonyms: N-METHYL-3-AMINO-1,2-PROPANEDIOL;3-(AMINOMETHYL)-1,2-PROPANEDIOL;3-METHYLAMINO-PROPANE-1,2-DIOL;3-METHYLAMINO-1,2-PROPANEDIOL;2,3-Dihydroxy-N-methylpropylamine;3-Methylamino-1,2-Propandiol;N-Methyl-2,3-dihydroxypropylamine;1,2-Propanediol, 3-(methylamino)-
• CAS NO: 40137-22-2
• Molecular Formula: C₄H₁₁NO₂
• Molecular Weight: 105.14
• EINECS: 254-809-0
• Product Categories: API;Amino Alcohols;Organic Building Blocks;Oxygen Compounds
• Mol File: 40137-22-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 69°C (estimate)
• Boiling Point: 247 °C
• Flash Point: 152 °C
• Appearance: clear colorless to pale yellow viscous liquid
• Density: 1.095 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00467mmHg at 25°C
• Refractive Index: n20/D 1.476
• Storage Temp.: Store below +30°C.
• PKA: 14.09±0.20(Predicted)
• Water Solubility: miscible
• BRN: 1733341
• CAS DataBase Reference: 3-Methylamino-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylamino-1,2-propanediol(40137-22-2)
• EPA Substance Registry System: 3-Methylamino-1,2-propanediol(40137-22-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: 2735
• WGK Germany: 3
• F: 3-10-34
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 40137-22-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H11NO2/c1-5-2-4(7)3-6/h4-7H,2-3H2,1H3/p+1/t4-/m1/s1

Synthetic route

oxiranyl-methanol (556-52-5) + methylamine (74-89-5) → 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
at 55℃; under 225.023 - 31503.2 Torr; for 0.666667h; Pressure; Autoclave; Green chemistry;	98.99%
In water at 30℃; for 4 - 5h;	92.7%
unter Kuehlung;

potassium N-(1,2-dihydroxypropyl)-N-methylamidosulfonate → 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
With sulfuric acid; water at 100℃; for 8h; Hydrolysis;	95%

3-monochloro-1,2-propanediol (96-24-2) + methylamine (74-89-5) → 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
With sodium hydroxide In water at 17 - 42℃; for 0.270167h;	82.4%
With sodium hydrogencarbonate; sodium hydroxide In water at 50 - 65℃; under 1125.11 Torr; for 4.33333h; Product distribution / selectivity;

oxiranyl-methanol (556-52-5) + methylamine (74-89-5) → 3-methylamino-propane-1,2-diol (40137-22-2) + 2-(methylamino)-1,3-propanediol (77697-86-0)

3-(N-Benzyl-N-methylamino)-1,2-propanediol (60278-98-0) → 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
With hydrogen
With hydrogen; palladium on activated charcoal In methanol under 2585.7 Torr; for 18h;

N,N'-bis(2,3-dihydroxypropyl)-5-{2-[(2,3-dihydroxypropyl)methylamino]-2-oxoethoxy}-1,3-benzenedicarboxamide (193483-80-6) → 3-methylamino-propane-1,2-diol (40137-22-2) + [3,5-Bis-(2,3-dihydroxy-propylcarbamoyl)-phenoxy]-acetic acid

Conditions	Yield
With water at 95℃; Rate constant;

oxiranyl-methanol (556-52-5) → 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
In water; methylamine
With methylamine In water	25.6g (76%)

1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-methylmethanamine → 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
With carbon dioxide; water at 140℃; under 22502.3 Torr; for 12h; Autoclave;

3-methylamino-propane-1,2-diol (40137-22-2) + (2′Z-3′E)-6-bromoindirubin-3′-[O-(2-bromoethyl)oxime] (1067884-35-8) → (2'Z-3'E)-6-bromoindirubin-3'-(O-{2-[N-methyl,N-(2,3-dihydroxypropyl)amino]ethyl}oxime) (1067884-44-9)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃;	100%
In N,N-dimethyl-formamide at 90℃; for 0.666667h; Inert atmosphere; Microwave irradiation;

3-methylamino-propane-1,2-diol (40137-22-2) → sodium 1-(N-methyl-N-2,3-dihydroxypropyl)diazen-1-ium-1,2-diolate

Conditions	Yield
With nitrogen(II) oxide; sodium methylate In methanol; diethyl ether at 20℃; under 4654.46 Torr;	98.9%
With nitrogen(II) oxide; sodium methylate In methanol; diethyl ether

Na2CO3.10H2O + 5-Acetoxyacetylamino-2,4,6-tribromo-3-[N-(2,3-diacetoxypropyl)carbamoyl] benzoyl chloride (403695-94-3) + 3-methylamino-propane-1,2-diol (40137-22-2) → 5-acetoxyacetylamino-2,4,6-tribromo-N,N'-bis-(2,3-diacetoxypropyl)-N-methylisophthalamide

Conditions	Yield
In acetone	98%

3-methylamino-propane-1,2-diol (40137-22-2) + 5-methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-diacetoxypropyl)amide chloride (150928-21-5) → 5-methoxyacetylamino-2,4,6-triiodoisophthalic acid [(2,3-dihydroxy-N-methylpropyl)-(2,3-diacetoxypropyl)]diamide (1193076-40-2)

Conditions	Yield
With triethylamine In N,N-dimethyl acetamide Product distribution / selectivity;	98%
With triethylamine In ISOPROPYLAMIDE at 20℃; for 2h;

ethyl 1-imidazolecarboxylate (19213-72-0) + 3-methylamino-propane-1,2-diol (40137-22-2) → 5‐(hydroxymethyl)‐3‐methyl‐1,3‐oxazolidin‐2‐one

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 15h; Reflux;	98%

3-methylamino-propane-1,2-diol (40137-22-2) + (R)-1-(3-((3'-(3-bromopropoxy)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)oxy)propyl)pyrrolidin-3-ol + trifluoroacetic acid (76-05-1) → 3-((3-((3'-(3-((R)-3-hydroxypyrrolidin-1-yl)propoxy)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)oxy)propyl)(methyl)amino)propane-1,2-diol trifluoroacetate

Conditions	Yield
Stage #1: 3-methylamino-propane-1,2-diol; (R)-1-(3-((3'-(3-bromopropoxy)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)oxy)propyl)pyrrolidin-3-ol With N-ethyl-N,N-diisopropylamine In methanol at 65℃; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile	98%

3-methylamino-propane-1,2-diol (40137-22-2) + 3,3'-bis(3-bromopropoxy)-2,2'-dimethyl-1,1'-biphenyl → 3,3'-((((2,2'-dimethyl-[1,1'-biphenyl]-3,3'-diyl)bis(oxy))bis(propane-3,1-diyl))bis(methylazanediyl))bis(propane-1,2-diol)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at 65℃; for 72h; Inert atmosphere;	98%

5-Amino-3-acetoxymethyl-2,4,6-triiodobenzoyl chloride (250781-45-4) + 3-methylamino-propane-1,2-diol (40137-22-2) → 5-Amino-3-acetoxymethyl-N-methyl-N-(2,3-dihydroxypropyl)-2,4,6-triiodo-benzamide

Conditions	Yield
	97%
	97%

Na2CO3.10H2O + 5-acetoxyacetylamino-2,4,6-tribromo-3-carbamoylbenzoyl chloride (403696-08-2) + 3-methylamino-propane-1,2-diol (40137-22-2)

Conditions	Yield
In acetone	97%

Conditions	Yield
With sulfuric acid; water at 100℃; for 8h; Hydrolysis;	95%

Na2CO3.10H2O + 2,4,6-tribromo-5-bromomethanesulfonylamino-3-[N-(2,3-diacetoxypropyl)carbamoyl]benzoyl chloride + 3-methylamino-propane-1,2-diol (40137-22-2) → 2,4,6-Tribromo-5-bromomethanesulfonylamino-N-(2,3-dihydroxypropyl)-N-methyl-N'-(2,3-diacetoxypropyl)-isophthalamide (403696-05-9)

Conditions	Yield
In acetone	95%

3-methylamino-propane-1,2-diol (40137-22-2) + 1,3-dimethyl 5-(2-methoxyacetamido)-2,4,6-triiodoisophthalate → 3-[(2,3-dihydroxypropylaminoformyl)]-2,4,6-triiodo-5-[(methoxyacetyl)amino]benzoic acid methyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane for 18h; Reflux; Large scale;	95%

3-methylamino-propane-1,2-diol (40137-22-2) + 3-[(2,3-dihydroxypropylaminoformyl)]-2,4,6-triiodo-5-[(methoxyacetyl)amino]benzoic acid methyl ester → iopromide (73334-07-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine Large scale;	95%

3-methylamino-propane-1,2-diol (40137-22-2) + 3-[(2,3-dihydroxypropylaminoformyl)]-5-[(methoxyacetyl)amino]benzoic acid methyl ester → C18H27N3O8 (1009809-16-8)

Conditions	Yield
With sodium t-butanolate In methanol for 48h; Reagent/catalyst; Reflux;	92.3%

3-methylamino-propane-1,2-diol (40137-22-2) + 5-methoxyacetamido-3-allylcarbamoyl-2,4,6-triiodobenzoyl chloride → 5-methoxyacetamido-2,4,6-triiodophthalic acid [(allylamino)-(2,3-dihydroxy-N-methylpropyl)]diamide

Conditions	Yield
In 1,4-dioxane; acetonitrile at 20℃;	91%
In 1,4-dioxane; acetonitrile at 20℃;	60 g

3-methylamino-propane-1,2-diol (40137-22-2) + 3-nitro-5-(((2-oxo-1,3-dioxolan-4-yl)methyl)carbamoyl)benzoic acid → N1-(2,3-dihydroxypropyl)-N1-methyl-5-nitro-N3-((2-oxo-1,3-dioxolan-4-yl)methyl)isophthalamide

Conditions	Yield
Stage #1: 3-nitro-5-(((2-oxo-1,3-dioxolan-4-yl)methyl)carbamoyl)benzoic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h; Stage #2: 3-methylamino-propane-1,2-diol In ethanol; dichloromethane at -10℃; for 2.5h;	90%

3-methylamino-propane-1,2-diol (40137-22-2) + 5-methoxyacetamido-2,4,6-triiodoisophthalic acid [(2-oxo-1,3-dioxolan-4-yl)methyl]amide chloride → 5-methoxyacetamido-2,4,6-triiodoisophthalic acid {[(2-oxo-1,3-dioxolan-4-yl)methyl]-(2,3-dihydroxy-N-methylpropyl)}diamide

Conditions	Yield
With triethylamine In N,N-dimethyl acetamide at 20℃; for 10h;	90%
With triethylamine In N,N-dimethyl acetamide at 20℃; for 10h;	90%

5-nitro-1,3-benzenedicarboxylic acid, monomethyl ester (1955-46-0) + 3-methylamino-propane-1,2-diol (40137-22-2) → 3-((2,3-dihydroxypropyl)methylcarbamoyl)-5-nitrobenzoic acid

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol Inert atmosphere; Reflux;	89%
In acetonitrile at 75 - 80℃; for 5h;	80%

3-methylamino-propane-1,2-diol (40137-22-2) + C23H26O8 → C27H37NO10

Conditions	Yield
In dichloromethane for 0.5h;	88.9%

2-chloro-6-methoxy-3-nitropyridine (38533-61-8) + 3-methylamino-propane-1,2-diol (40137-22-2) → 3-[(6-methoxy-3-nitro-pyridin-2-yl)methyl-amino]propane-1,2-diol (677277-91-7)

Conditions	Yield
In ethanol for 2h; Heating / reflux;	87.1%

3-methylamino-propane-1,2-diol (40137-22-2) + [(3-acetoxy-1-acetylindol-2-yl)methylene]malononitrile (1431945-57-1) → 1-acetyl-2-[2-cyano-2-(5-hydroxymethyl-3-methyloxazolidin-2-ylidene)ethylidene]indolin-3-one (1431945-58-2)

Conditions	Yield
In isopropyl alcohol for 1h; Reflux;	86.7%

5-Methoxyacetamido-2,4,6-triiodoisophthaloyl chloride (76350-03-3) + 3-methylamino-propane-1,2-diol (40137-22-2) → 5-[(2-methoxy)acetamido]-3-(2,3-dihydroxy-N-propyl(methyl)carbamoyl)-2,4,6-triiodobenzoyl chloride

Conditions	Yield
With ZrO2-Cr2O3 solid base catalyst In N,N-dimethyl acetamide at 10 - 15℃; for 5h;	85%

3-methylamino-propane-1,2-diol (40137-22-2) + α-isocyanato-L-O-methyltyrosine methyl ester (52177-38-5) → (2RS)-<<(2,3-dihydroxypropyl)methylamino>carbonyl>-O-methyltyrosine methyl ester (114359-43-2)

Conditions	Yield
In 1,4-dioxane 1.) 0 deg C, 1 h, 2.) RT, 1 h;	84%

3-methylamino-propane-1,2-diol (40137-22-2) + tert-butyl 1H-imidazole-1-carboxylate (49761-82-2) → C5H9NO3

Conditions	Yield
With potassium hydroxide In toluene Heating;	82%

(3E)-5,6-difluoro-3-[4-(6-fluoropyridin-3-yl)-5,5-dimethylfuran-2(5H)-ylidene]-1,3-dihydro-2H-indol-2-one + 3-methylamino-propane-1,2-diol (40137-22-2) → (3E)-3-[4-{6-[(2,3-dihydroxypropyl)(methyl)amino]pyridin-3-yl}-5,5-dimethylfuran-2(5H)-ylidene]-5,6-difluoro-1,3-dihydro-2H-indol-2-one

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 16h;	82%

4-[(5E)-5-(5,6-difluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2,2-dimethyl-2,5-dihydrofuran-3-yl]benzoic acid + 3-methylamino-propane-1,2-diol (40137-22-2) → 4-[(5E)-5-(5,6-difluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2,2-dimethyl-2,5-dihydrofuran-3-yl]-N-(2,3-dihydroxypropyl)-N-methylbenzamide

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 0.166667h;	81%

4-methyleneoxetan-2-one (674-82-8) + 3-methylamino-propane-1,2-diol (40137-22-2) → N-(2,3-dihydroxypropyl)-3-oxobutanamide (160173-41-1)

Conditions	Yield
In tetrahydrofuran at -5 - 0℃; for 1h;	79%

3-methylamino-propane-1,2-diol (40137-22-2) + 4-[(3-bromophenyl)-amino]-6-fluoropyrido[3,4-d]pyrimidine (171179-03-6) → 4-[(3-Bromophenyl)amino]-6-[N-(2,3-dihydroxy-propyl) methylamino]pyrido[3,4-d]pyrimidine

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 24h;	72%

Upstream product

• 556-52-5 oxiranyl-methanol 
• 74-89-5 methylamine 
• 96-24-2 3-monochloro-1,2-propanediol 
• 97546-81-1 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-methylmethanamine 
• 193483-80-6 N,N'-bis(2,3-dihydroxypropyl)-5-{2-[(2,3-dihydroxypropyl)methylamino]-2-oxoethoxy}-1,3-benzenedicarboxamide 
• 60278-98-0 3-(N-Benzyl-N-methylamino)-1,2-propanediol 

Downstream Products

• 114359-43-2 (2RS)-<<(2,3-dihydroxypropyl)methylamino>carbonyl>-O-methyltyrosine methyl ester 
• 73334-07-3 iopromide 
• 403696-05-9 2,4,6-Tribromo-5-bromomethanesulfonylamino-N-(2,3-dihydroxypropyl)-N-methyl-N'-(2,3-diacetoxypropyl)-isophthalamide 
• 403695-79-4 N,N'-bis-[2,4,6-tribromo-3-[N-(2,3-dihydroxypropyl)-N-methylcarbamoyl]-5-[N-(2,3-dihydroxypropyl)carbamoyl]phenyl]malonamide 
• 946506-30-5 acetic acid {3-chlorocarbonyl-5-[(2,3-dihydroxy-propyl)-methyl-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester 
• 1125455-31-3 4-({3-chloro-4-[(1-ethyl-4,5-dimethyl-1H-imidazol-2-yl)thio]phenyl}amino)-7-{3-[(2,3-dihydroxypropyl)(methyl)amino]propoxy}-6-methoxyquinoline-3-carbonitrile 
• 1186057-92-0 5-(N-(3-(N-(3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodophenyl)acetamido)-2-hydroxypropyl)acetamido)-N₁-(2,3-dihydroxypropyl)-2,4,6-triiodo-N₃-methoxyisophthalamide 
• 1186057-88-4 5,5'-(2-hydroxypropane-1,3-diyl)bis(acetylazanediyl)bis(N₁,N₃-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-N₁,N₃-dimethylisophthalamide) 
• 1447756-07-1 C₁₅H₁₇F₂N₃O₅ 

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