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738-70-5

Basic Information
CAS No.: 738-70-5
Name: Trimethoprim
Molecular Structure:
Molecular Structure of 738-70-5 (Trimethoprim)
Formula: C14H18N4O3
Molecular Weight: 290.32
Synonyms: Bacidal;Sulthrim;Bactrim;Resprim Forte;Trimetoprim [DCIT];Deprim;5-(3,4,5-Trimethoxybenzyl)-2,4-diaminopyrimidine;Briscotrim;Salvatrim;Metoprim;Bacdan;Abaprim;Bencole;Bacticel;Trimez-IFSA;Trimethopim(TMP);Sulfamethoxazole Trimethoprim;Bethaprim;Trimexol;Sulfamethoprim;Streptoplus;Trimethoprim [USAN:BAN:INN:JAN];5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;Tmp Smx;Trimethoprime [INN-French];NIH 204;Wellcoprin;Roubal;Trimpex (TN);Co-Trimoxizole;Trimetoprima [INN-Spanish];Syraprim;Monotrimin;Protrin;2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine;
EINECS: 212-006-2
Density: 1.252 g/cm3
Melting Point: 199-203 °C
Boiling Point: 525.956 °C at 760 mmHg
Flash Point: 271.889 °C
Solubility: Soluble in DMSO
Appearance: Odorless white powder.
Hazard Symbols: ToxicT
Risk Codes: 25
Safety: 45
Transport Information: UN 3249
PSA: 105.51000
LogP: 2.42000
Synthetic route
30078-48-9

3-anilino-2-(3,4,5-trimethoxybenzyl)propenenitrile

506-93-4

guanidine nitrate

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Stage #1: guanidine nitrate With sodium methylate at 30℃; for 0.5h; Reflux;
Stage #2: 3-anilino-2-(3,4,5-trimethoxybenzyl)propenenitrile for 10h; Reflux;
95%

β-(p-methylanilino)-β-3,4,5-trimethoxybenzylacrylonitrile

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
90%
55694-05-8

2,4-dichloro-5-(3,4,5-trimethoxybenzyl)pyrimidine

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With ammonia In methanol at 175℃; for 6h;85%
With ammonia In ethanol at 120℃; for 12h;83%
39667-16-8

6-methylsulfanyl-5-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4-diamine

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With Raney nickel W-5 In ethanol; 2-methoxy-ethanol; water at 120℃; for 1h;83%
21253-58-7

2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl)pyrimidine

74-88-4

methyl iodide

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With sodium methylate In dimethyl sulfoxide for 4h; Ambient temperature;66%
55694-05-8

2,4-dichloro-5-(3,4,5-trimethoxybenzyl)pyrimidine

A

2-Chloro-5-(3,4,5-trimethoxy-benzyl)-pyrimidin-4-ylamine

B

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With ammonia In ethanol at 120℃; for 8h;A 22%
B 55%
7520-69-6, 141292-62-8

3,4,5-trimethoxy-2'-(methoxymethyl)cinnamonitrile

124-41-4

sodium methylate

593-85-1

diguanidine carbonate

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
1) DMSO, 70 to 75 deg C, 1.0 h, 2) DMSO, 110 deg C, 1.0 h; Yield given. Multistep reaction;
50-01-1

guanidine hydrochloride

3-methylthio-2-(3',4',5'-trimethoxybenzyl)acrylonitrile

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With sodium ethanolate 1.) ethanol, RT, 20 min, 2.) ethanol, reflux, 12 h; Yield given. Multistep reaction;
30563-87-2

2,4-diamino-5-(3,4,5-trimethoxybenzyl)-6-chloropyrimidine

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal In water
30077-81-7

3-morpholino-5-(3',4',5'-trimethoxybenzyl)acrylopyrimidine

113-00-8

guanidine nitrate

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
In ethanol; dimethyl sulfoxide for 18h; Heating;
With dimethyl sulfoxide In ethanol
86-81-7

3,4,5-trimethoxy-benzaldehyde

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOMe / dimethylsulfoxide
2: DMSO / ethanol
View Scheme
Multi-step reaction with 5 steps
1: 95 percent / TEBA / 1 h / 85 °C
2: 90 percent / H2 / 10 percent Pd/C / ethyl acetate / 2.5 h
3: Na / methanol / 12 h / Heating
4: PCl5; POCl3 / 4 h / Heating
5: H2; AcOH / 10 percent Pd/C / H2O
View Scheme
Multi-step reaction with 4 steps
1.1: sodium methylate; 15-crown-5 / dimethyl sulfoxide / 2.5 h / 105 °C
2.1: water; sodium tetrahydroborate / 1 h / 20 °C
3.1: acetic anhydride / N,N-dimethyl-formamide / 1 h / Reflux
3.2: 1 h / Reflux
4.1: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 1 h / 0 - 25 °C
4.2: 1.5 h / 25 - 30 °C
View Scheme
910859-93-7

diethyl 3,4,5-trimethoxybenzyl phosphate

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: i-PrMgCl*LiCl / tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / 0 °C
1.2: CuBr; P(OEt)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.17 h / -15 °C
1.3: 81 percent / tetrabutylammonium iodide / tetrahydrofuran; 1,2-dimethoxy-ethane / 1.5 h / 60 °C
2.1: 87 percent / aq. HCl / methanol / 0.25 h / 20 °C
3.1: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C
4.1: 85 percent / NH3 / methanol / 6 h / 175 °C
View Scheme
93885-69-9

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4(1H,3H)-dione

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C
2: 85 percent / NH3 / methanol / 6 h / 175 °C
View Scheme
910859-94-8

2,4-di-tert-butoxy-5-(3,4,5-trimethoxybenzyl)pyrimidine

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / aq. HCl / methanol / 0.25 h / 20 °C
2: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C
3: 85 percent / NH3 / methanol / 6 h / 175 °C
View Scheme
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 83 percent / DMAP; Et3N / tetrahydrofuran / 4 h / 20 °C
2.1: i-PrMgCl*LiCl / tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / 0 °C
2.2: CuBr; P(OEt)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.17 h / -15 °C
2.3: 81 percent / tetrabutylammonium iodide / tetrahydrofuran; 1,2-dimethoxy-ethane / 1.5 h / 60 °C
3.1: 87 percent / aq. HCl / methanol / 0.25 h / 20 °C
4.1: 86 percent / N,N-dimethylbenzenamine; POCl3 / 1 h / 110 °C
5.1: 85 percent / NH3 / methanol / 6 h / 175 °C
View Scheme
29958-02-9

2-cyano-3-(3,4,5-trimethoxy-phenyl)propionic acid ethyl ester

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Na / methanol / 12 h / Heating
2: PCl5; POCl3 / 4 h / Heating
3: H2; AcOH / 10 percent Pd/C / H2O
View Scheme
37389-83-6

2,4-diamino-5-(3',4',5'-trimethoxy-benzyl)-6-hydroxy-pyrimidine

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PCl5; POCl3 / 4 h / Heating
2: H2; AcOH / 10 percent Pd/C / H2O
View Scheme
Stage #1: 2,4-diamino-5-(3',4',5'-trimethoxy-benzyl)-6-hydroxy-pyrimidine With triethylamine; p-toluenesulfonyl chloride In dichloromethane at 0 - 25℃; for 1h;
Stage #2: With sodium tetrahydroborate In dichloromethane at 25 - 30℃; for 1.5h;
350986-48-0

(Z)-β-(3,4,5-trimethoxyphenyl) α-cyano propenoic acid

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / H2 / 10 percent Pd/C / ethyl acetate / 2.5 h
2: Na / methanol / 12 h / Heating
3: PCl5; POCl3 / 4 h / Heating
4: H2; AcOH / 10 percent Pd/C / H2O
View Scheme
5320-31-0

3,4,5-trimethoxyphenylacetaldehyde

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99.5 percent / n-BuLi / tetrahydrofuran; hexane / 14 h / Ambient temperature
2: 73.6 percent / POCl3 / 14 h / Ambient temperature
3: 100 percent / NH2OH*HCl, AcONa / ethanol / 14 h / Ambient temperature
4: 93.5 percent / Ac2O / 2 h / Heating
5: 1.) NaOEt / 1.) ethanol, RT, 20 min, 2.) ethanol, reflux, 12 h
View Scheme

1-methylthio-3-(3',4',5'-trimethoxyphenyl)propene

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73.6 percent / POCl3 / 14 h / Ambient temperature
2: 100 percent / NH2OH*HCl, AcONa / ethanol / 14 h / Ambient temperature
3: 93.5 percent / Ac2O / 2 h / Heating
4: 1.) NaOEt / 1.) ethanol, RT, 20 min, 2.) ethanol, reflux, 12 h
View Scheme

3-methylthio-2-(3',4',5'-trimethoxybenzyl)acrolein

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / NH2OH*HCl, AcONa / ethanol / 14 h / Ambient temperature
2: 93.5 percent / Ac2O / 2 h / Heating
3: 1.) NaOEt / 1.) ethanol, RT, 20 min, 2.) ethanol, reflux, 12 h
View Scheme

3-methylthio-2-(3',4',5'-trimethoxybenzyl)acrolein oxime

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93.5 percent / Ac2O / 2 h / Heating
2: 1.) NaOEt / 1.) ethanol, RT, 20 min, 2.) ethanol, reflux, 12 h
View Scheme
86-81-7

3,4,5-trimethoxy-benzaldehyde

3.4.5-trimethoxy-benzoic acid-<3.4.5-trimethoxy-benzoylidenehydrazide>

3.4.5-trimethoxy-benzoic acid-<3.4.5-trimethoxy-benzoylidenehydrazide>

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 1 h
2: 79 percent / triethylsilane / trifluoroacetic acid / Ambient temperature
3: 83 percent / ammonia / ethanol / 12 h / 120 °C
View Scheme
Multi-step reaction with 3 steps
1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 1 h
2: 79 percent / triethylsilane / trifluoroacetic acid / Ambient temperature
3: 55 percent / ammonia / ethanol / 8 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: 82 percent / methanol / Ambient temperature
2: 1) DMSO, 70 to 75 deg C, 1.0 h, 2) DMSO, 110 deg C, 1.0 h
View Scheme
148256-84-2

2,4-dichloro-5-[hydroxy-(3,4,5-trimethoxyphenyl)methyl]pyrimidine

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / triethylsilane / trifluoroacetic acid / Ambient temperature
2: 83 percent / ammonia / ethanol / 12 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: 79 percent / triethylsilane / trifluoroacetic acid / Ambient temperature
2: 55 percent / ammonia / ethanol / 8 h / 120 °C
View Scheme
39667-14-6

2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethane-1,2-diol / 120 - 160 °C
2: 1.) NaOMe / 1.) DMSO
3: 83 percent / Raney nickel W-5 / 2-methoxy-ethanol; H2O; ethanol / 1 h / 120 °C
View Scheme
39667-15-7

4-(2,4-Diamino-6-methylsulfanyl-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenol

738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaOMe / 1.) DMSO
2: 83 percent / Raney nickel W-5 / 2-methoxy-ethanol; H2O; ethanol / 1 h / 120 °C
View Scheme
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554-68-7
30806-86-1
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    Technical Data Sheet Chemical name: 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine Moleculor Formula : C14H18N4O3 Molecular Weight:: 290.32 CAS#: 738-70-5 EINECS: 212-006-2 Appearance:white powder Storage:cool and dry Package:25kg 10kg

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    CAS:738-70-5 Trimethoprim

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    Chemical Name: Trimethoprim (TMP) Other name: Abaprim;5-((3,4,5-trimethoxyphenyl)methyl)-2,4-pyrimidinediamine;5-(3,4,5-trimethoxybenzyl)-2,4-diaminopyrimidine CAS: 738-70-5 EINECS No.: 212-006-2 Formula: C14H18N4O3 Molecular Weight: 29

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    Trimethoprim Chemical Name: Trimethoprim (TMP) Other name: Abaprim;5-((3,4,5-trimethoxyphenyl)methyl)-2,4-pyrimidinediamine;5-(3,4,5-trimethoxybenzyl)-2,4-diaminopyrimidine CAS: 738-70-5 EINECS No.: 212-006-2 Formula: C14H18N4O3 Molec

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Chemistry

FOMULA: C14H18N4O
Mol. mass: 290.32 g/mol 
EINECS: 212-006-2 
Index of Refraction: 1.608
Molar Refractivity: 80.25 cm3
Molar Volume: 231.8 cm3
Surface Tension: 53.9 dyne/cm
Density: 1.252 g/cm3
Flash Point: 271.9 °C
Enthalpy of Vaporization: 80.02 kJ/mol
Boiling Point: 526 °C at 760 mmHg
Vapour Pressure: 3.74E-11 mmHg at 25°C 
Storage temp of Trimethoprim is 2-8°C.Trimethoprim,its melting point is about  199-203 °C;appearance is white powder|
Stability: Stable. Incompatible with strong oxidizing agents, acids
Water solubility is less than 0.1 g/100 mL at 24 oC
Product Categories: Pharmaceutical;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Peptide Synthesis/Antibiotics
 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) belongs to the class of chemotherapeutic agents known as dihydrofolate reductase inhibitors. It was formerly marketed by GlaxoSmithKline under trade names including Monotrim,  Proloprim and Triprim.In clinical use it is often abbreviated TRI or TMP; its common laboratory abbreviation is W.
Following is the molecular structure of 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5):

 

History

Since 1980 in the UK,Trimethoprim was used as monotherapy,it is indicated for the prophylaxis and treatment of urinary tract infections. Co-trimoxazole, with its greater efficacy against a limited number of bacteria, remains indicated for some infections.

Uses

 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) is a bacteriostatic antibiotic mainly used in the prophylaxis and treatment of urinary tract infections. It was commonly used in a 1:5 combination with Sulfamethoxazole , a sulfonamide antibiotic , which inhibits an earlier step in the folate synthesis pathway.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 90mg/kg (90mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Chemotherapy Vol. 14, Pg. 37, 1969.
 
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998.
mouse LD50 intravenous 132mg/kg (132mg/kg)   Journal of Chemotherapy. Vol. 5, Pg. 400, 1993.
 
mouse LD50 oral 2764mg/kg (2764mg/kg)   United States Patent Document. Vol. #4180578,
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
rat LD50 intraperitoneal 500mg/kg (500mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998.
rat LD50 oral > 5300mg/kg (5300mg/kg)   Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
women TDLo oral 56mg/kg/7D-I (56mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

BLOOD: OTHER CHANGES

MUSCULOSKELETAL: JOINTS
Postgraduate Medical Journal. Vol. 68, Pg. 391, 1992.
women TDLo oral 60mg/kg/10D-I (60mg/kg) BLOOD: THROMBOCYTOPENIA New Zealand Medical Journal. Vol. 106, Pg. 251, 1993.
 

Safety Profile

Hazard Codes: ToxicT
Risk Statements: 25 
R25: Toxic if swallowed
Safety Statements: 45 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 3249
WGK Germany: 3
RTECS: UV8225000
F: 8-10-21 
F 8: Photosensitive
F 10: Keep under argon
F 21: Sensitive to humidity
HazardClass: 6.1(b)
PackingGroup: III 
Use of 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) is contraindicated during pregnancy, especially the first trimester, and for sufferers of certain blood disorders. It is contraindicated to use trimethoprim during pregnancy, especially the first trimester, and for sufferers of certain blood disorders. 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) also may be involved in a reaction similar to disulfiram when alcohol is consumed after it is used, particularly when used in combination with sulfamethoxazole .It can also reduce clearance of creatinine at renal tubules.

Specification

Tetrahydrofolic acid is an essential precursor in the de novo synthesis of the intermediate THYMIDINE monophoshpate (dTMP), precursor of DNA metabolite THYMIDINE triphosphate. 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) is also called as Trimethoprim ; Bactrim ; Bactrim ; Cotrim ; SMZ/TMP ; Septra ; Sulfatrim ; 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)- ; 5-((3,4,5-Trimethoxyphenyl)methyl)-2,4-pyrimidinediamine ; 5-25-13-00429 (Beilstein Handbook Reference) ; Abaprim ; Anitrim ; BRN 0625127 ; Bacidal ; Bacticel ; CCRIS 2410 ; Co-Trimoxizole ; Cotrimel ; EINECS 212-006-2 ; Espectrin ; Fortrim ; Kombinax ; Monoprim ; Pancidim ; Resprim Forte ; Sinotrim ; Sulmeprim ; Trimethoprime [INN-French] ; UNII-AN164J8Y0X ; Velaten ; component of Bactrim and so on.