Home Cart 0 Sign in  
X

[ CAS No. 183610-70-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 183610-70-0
Chemical Structure| 183610-70-0
Chemical Structure| 183610-70-0
Structure of 183610-70-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 183610-70-0 ]

Related Doc. of [ 183610-70-0 ]

Alternatived Products of [ 183610-70-0 ]

Product Details of [ 183610-70-0 ]

CAS No. :183610-70-0 MDL No. :MFCD04972538
Formula : C6H5F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :YWOWJQMFMXHLQD-UHFFFAOYSA-N
M.W : 162.11 Pubchem ID :2760920
Synonyms :

Safety of [ 183610-70-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 183610-70-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 183610-70-0 ]
  • Downstream synthetic route of [ 183610-70-0 ]

[ 183610-70-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 65753-52-8 ]
  • [ 183610-70-0 ]
YieldReaction ConditionsOperation in experiment
95% With ammonia In water at 130℃; for 10 h; 750 g of 2-fluoro-3-trifluoromethylpyridine was added to the ammoniation reactor.700g of water was added to the ammoniation reactor, and then 250g of liquid ammonia was fed to the ammoniation reactor.Raise temperature to 130°C, pressure not more than 3.0MPa, react for 10 hours,Cool down to 90 °C, discharge to the receiving kettle, receive cooling down to 10 °C,2-Amino-3-trifluoromethylpyridine is obtained by centrifugation and drying; the yield is about 95percent
Reference: [1] Patent: CN108003093, 2018, A, . Location in patent: Paragraph 0008; 0017-0018; 0020-0021; 0023-0024
  • 2
  • [ 911112-72-6 ]
  • [ 183610-70-0 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 5 - 23℃; for 0.5 h;
Stage #2: With sodium hydroxide In water at 0℃;
Step 2) 3-Trifluoromethyl-pyridin-2-ylamine CAS-No. [183610-70-0]; To conc. sulfuric acid (230 mL) at 5° C. was dropwise added above (4-methoxy-benzyl)-(3-trifluoromethyl-pyridin-2-yl)-amine (83.76 g, 297 mmol) keeping the internal temperature below 20° C., stirring was continued at 23° C. for 30 min. Poured onto ice, made alkaline with 32percent NaOH-sol. (ca. 800 mL) with external ice cooling, saturated with solid NaCl, extracted twice with THF/TBME/DCM, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a white solid (44.27 g, 92percent). MS (ISP) 163.2 [(M+H)+].
Reference: [1] Patent: US2007/72879, 2007, A1, . Location in patent: Page/Page column 18
  • 3
  • [ 65753-47-1 ]
  • [ 183610-70-0 ]
Reference: [1] Journal of Fluorine Chemistry, 1999, vol. 93, # 2, p. 153 - 157
[2] Patent: EP1790650, 2007, A1, . Location in patent: Page/Page column 54
[3] Patent: CN108003093, 2018, A,
  • 4
  • [ 67-56-1 ]
  • [ 143812-76-4 ]
  • [ 183610-70-0 ]
  • [ 177211-80-2 ]
Reference: [1] Chemical Communications, 1996, # 7, p. 813 - 814
  • 5
  • [ 183610-70-0 ]
  • [ 22245-83-6 ]
Reference: [1] Patent: CN108003093, 2018, A, . Location in patent: Paragraph 0008; 0017-0019; 0020-0022; 0023-0025
  • 6
  • [ 183610-70-0 ]
  • [ 79456-34-1 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In acetonitrile at 5 - 23℃; for 1 h; Step 3) 5-Bromo-3-trifluoromethyl-pyridin-2-ylamine CAS-No. [79456-34-11; To a solution of the above 3-trifluoromethyl-pyridin-2-ylamine (16.21 g, 100 mmol) in acetonitrile (300 mL) at 5° C. was added NBS (17.8 g, 100 mmol) and the mixture was stirred at 23° C. for 1 h. Poured into ice and additional sat. NaHCO3-sol., extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a yellow solid, which was filtered through a silica gel and cotton wool column with dichloromethane to give the title compound as a yellow solid (23.71 g, 98percent). MS (EI) 240.1 [(M)+], 242.0 [(M+2)+].
93% With N-Bromosuccinimide In acetonitrile at 20℃; Example 46; Preparation of iV-(5-(6-Amino-5-(trifluoromethyl)pyridin-3- yl)thiazolo [5,4-4. Insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with a 10percent- 30percent mixture of ethyl acetate and hexane. Concentration of appropriate fractions afforded the titled compound 5-Bromo-3- (trifluoromethyl)pyridin-2-amine (46B, 2.91 g, 93percent) as pale yellow crystalline solid. 1H NMR (300 MHz, CDCl3): δ 8.26 (d, 1 H, J = 1.9 Hz), 7.79 (d, 1 H, J = 1.9 Hz), 5.00 (br s, 2 H). MS (ES) [M+H] calc'd for C6H4BrF3N2 241; found 241.
89.7% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Compound BB-21-1 (42.0g, 259mmol) was dissolved in N, N - dimethylformamide (400mL), then was addedN - bromosuccinimide (46.1g, 259mmol).The reaction was stirred at 20 2 hours.The reaction solution was poured into stirred5percent mixture of sodium bisulfite and water (10:1), the precipitate was filtered, washed with water, dissolved in methylene chloride (a 500 mL), dried over sodium sulfatedrying, filtered, and concentrated to give the title compound BB -20-2 (yellow solid, 51.0g, yield: 89.7percent).
88% With N-Bromosuccinimide In N,N-dimethyl-formamide for 4 h; 2-Amino-3-trifluoromethyl pyridine (5.4 gm, 33.3 mmol) was dissolved in DMF (31 mL) and N-bromosuccinimide (5.9 gm, 33.3 mmol) dissolved in DMF (31 mL) was added <n="198"/>dropwise. The mixture was stirred for 4 hours, concentrated to ~ 20 mL and added dropwise into ice-water (600 mL). The product crashed out, was filtered, washed with water (100 mL) and dried under vacuum to afford 5-bromo-3-trifluoromethyl-pyridin-2-ylamine as a light brown solid (7.12 gm, 88percent). 1H NMR (d6-DMSO, 300 MHz) δ 8.22 (s, IH), 7.85 (s, IH), 6.66 (s, 2H); MS (ESI) m/z = 242.9 (MH+).
88% With N-Bromosuccinimide In acetonitrile at 0 - 23℃; for 4 h; N-bromosuccinimide (20.83g, 117.28 mmol) was portion wise added to a stirred solution of 3-(trifluoro- methyl)pyridin-2-amine (19g, 117.28 mmol) in MeCN (380 mL) at 0°C. The RM was stirred for4h at RT. The RM was quenched with aq. NaHCO3 solution (pH—8) and then filtered. The solid was washed with water (200 mL), and the product was dissolved with EtOAc (300 mL). The organic layer was dried over anhydr. Na2SO4, filtered and solvent was concentrated under reduced pressure to give 5-bromo-3-(trifluoromethyl)pyridin-2-amine (25g, 88percent) as a solid.
85% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; To a solution of 2-amino-3~trifluoromethylpyridine (100 g, 0.62 mol) in D F (500 mL) was added a solution of NBS (1 10 g, 0,62 mol) in DMF (500 mL) dropwise at room temperature. The solution was stirred at room temperature for 2 hours and then concentrated to 300 mL. The residue was added slowly to the beaker containing a mixture of 5percent aqueous NaHS03 and H20 (3 L, 1 :10 v/v). The precipitate was filtered, washed with H20 (2 x 500 mL) and dried under vacuum to give the title compound (120 g, 85percent) as a light brown solid.
84.6% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Example 1 l-ll-β-Chloro-6-furan-3-yl-8Arifluoromethyl4midazoll,2-a]pyridine-2-carbonyl)-piperidin-4- yl]-pyrrolidin-2-one (Compound 101) Step l 5-Bromo-3-trifluoromethyl-pyridin-2-ylamine[0102] A solution of N-Bromosuccinimide (54.89 g, 308.41 mmol) in DMF (250 niL) was rapidly added dropwise via addition funnel to a stirring solution of 2-Amino-3-(trifluoromethyl) pyridine (50.00 g, 308.41 mmol) in DMF (250 mL) at room temperature. The mixture was stirred for 2 hours, concentrated to a volume of 200 mL and added slowly into a beaker containing a cold stirring mixture of 5percent NaHSO3 and water (1.5 L, 1 :10 v/v). The precipitate was filtered, washed with water (3 x 500 mL) and dried under vacuum to afford 5-bromo-3- trifluoromethyl-pyridin-2-ylamine (62.89 g, 84.6percent) as a light brown solid. MS 242.9 (M+H+).
84.1% With N-Bromosuccinimide In acetonitrile at 0 - 25℃; for 2 h; The 3 - (trifluoromethyl) pyridin-2-amine (1.0g, 6 . 17mmol) dissolved in acetonitrile (30 ml) in, then dropped to 0 °C, then the NBS (1.2g, 6 . 74mmol) is slowly added to the system, is omitted, the temperature is increased to 25 °C reaction 2 hours. The concentrated, the residue by silica gel column chromatography (PE:EA=5:1) purification, to obtain the title compound (1.25g, yield 84.1percent).
82% With bromine In acetic acid at 25 - 30℃; 3-(Trifluoromethyl)-2-pyridinamine (150 g) was added to acetic acid (1500 mL) and stirred the mass for 10 to 15 min. Bromine (47.54 mL) was added to the mixture over a period of 45-60 min at 25-30°C. The reaction mass was maintained under stirring at 25-30°C for 2-3 h. After completion of the reaction, the mass was cooled to 10 to 15°C and diluted with water (2500 mL) subsequently neutralized the mass with solid sodium carbonate (420 g). The reaction mass was filtered and bed was washed with water (300 mL) and dried at 25 to 30°C for 12 h. The dried mass was dissolved in ethyl acetate (2250 mL) and washed with 5percent sodium bicarbonate solution (750 mL). The separated organic layer was washed with 10percent sodium chloride solution (750 mL). Clean organic layer was distilled out completely to obtain the title compound (183 g). Yield: 82percent Purity: 99.52percent 1H NMR (300 MHz, DMSO-<): δ 8.25 (s, 1H), 7.89 (s, 1H), 6.7 (bs, 2H). MS: m/z 242 (M+l)
81% With N-Bromosuccinimide In acetonitrile at 0 - 25℃; for 1 h; To a solution of 3-(trifluoromethyl)pyridin-2-amine (5.4 g, 33.3 mmol) in acetonitrile (100 mL) was added NBS (5.93 g, 33.3 mmol) at OeC and reaction mixture was stirred at 25eC for 1H. After completion of the reaction, reaction mixture was quenched with saturated sodium bicarbonate (25 mL) and extracted with EtOAc (25 mL/13). The combined organic phase was washed with brine (20 mL), dried over Na2S04, filtered. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 6.5 g (81percent) of the titled product. 1HNMR (400 MHz, DMSO-d6) U8.28 (d, J = 2.4 Hz, 1H), 7.91 (d, J = 2.4 Hz, 1H), 6.72 (s, 2H); ESI-MS (m/z) 241.08 (MH)\
74% at 20℃; for 2 h; 3-(trifluoromethyl)pyridin-2-amine (20 g, 123 mmol) was stirred in acetic acid (200 ml) at RT. Bromine (19.72 g, 123 mmol) was added drop wise with stirring. The reaction mixture was stirred for 2 h; followed by dilution with water. The product was extracted with ethyl acetate. Organic layer was washed with water, dried over sodium sulfate and concentrated to obtain the title product in 74percent yield.
3.8 g With N-Bromosuccinimide In N,N-dimethyl-formamide for 4 h; Cooling with ice Synthesis of 5-bromo-3-trifluoromethyl-pyridin-2-ylamine
To a stirred solution of R-10 (2.70 g, 16.66 mmol) in DMF (15 ml) is added N-bromosuccinimide (3.00 g, 16.85 mmol) as a DMF solution (15 ml, dropwise).
After 4 h the reaction is poured onto ice.
The resulting precipitate is collected via filtration to give the product as an off-white solid.
Dissolved into DCM and washed with brine.
The layers are separated and the organic phase is dried (MgSO4), filtered and concentrated to give the title intermediate (3.8 g); m/z 241.2/243.2 [M/M+2H].

Reference: [1] Patent: US2007/72879, 2007, A1, . Location in patent: Page/Page column 18
[2] Patent: WO2010/8847, 2010, A2, . Location in patent: Page/Page column 147
[3] Patent: CN105732602, 2016, A, . Location in patent: Paragraph 0364; 0366; 0367; 0368; 0369
[4] Patent: WO2009/23179, 2009, A2, . Location in patent: Page/Page column 196-197
[5] Patent: WO2015/158427, 2015, A1, . Location in patent: Page/Page column 87; 88
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 1078 - 1101
[7] Patent: WO2011/41713, 2011, A2, . Location in patent: Page/Page column 142
[8] Patent: WO2010/91411, 2010, A1, . Location in patent: Page/Page column 79
[9] Patent: CN105541792, 2016, A, . Location in patent: Paragraph 0454; 0455; 0456
[10] Patent: WO2015/145369, 2015, A1, . Location in patent: Page/Page column 36-37
[11] Patent: WO2018/20474, 2018, A1, . Location in patent: Page/Page column 314-315
[12] Patent: WO2012/7926, 2012, A1, . Location in patent: Page/Page column 49
[13] Patent: WO2008/12326, 2008, A1, . Location in patent: Page/Page column 69
[14] Patent: WO2010/139731, 2010, A1, . Location in patent: Page/Page column 135
[15] Patent: WO2012/24150, 2012, A1, . Location in patent: Page/Page column 135
[16] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4652 - 4656
[17] Patent: US2013/195879, 2013, A1, . Location in patent: Paragraph 0278; 0279
[18] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 507 - 512
[19] Patent: WO2007/134828, 2007, A1, . Location in patent: Page/Page column 68
[20] Patent: WO2008/138889, 2008, A2, . Location in patent: Page/Page column 85
[21] Patent: WO2008/138834, 2008, A1, . Location in patent: Page/Page column 89
[22] Patent: WO2010/139747, 2010, A1, . Location in patent: Page/Page column 102
  • 7
  • [ 183610-70-0 ]
  • [ 947249-01-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4652 - 4656
[2] Patent: WO2015/145369, 2015, A1,
[3] Patent: WO2007/134828, 2007, A1,
[4] Patent: WO2008/138834, 2008, A1,
[5] Patent: WO2008/138889, 2008, A2,
[6] Patent: WO2010/139747, 2010, A1,
  • 8
  • [ 183610-70-0 ]
  • [ 1121056-94-7 ]
YieldReaction ConditionsOperation in experiment
75% With sulfuric acid; nitric acid In water at 0 - 50℃; for 3.25 h; To a solution of 2-amino-3-(trifluoromethyl)pyridine (2 g, 12.34 mmol) in cone <n="242"/>sulfuric acid (10 mL) at 0 0C was added dropwise fuming nitric acid (0.56 mL, 12.34 mmol). After 15 min, the reaction was allowed to stir at room temperature. After 1 hour, the mixture was heated to 50 0C. After 2 hours, the reaction was cooled to room temperature and slowly poured into ice-water (200 mL). The precipitate was filtered and dried under high vacuum to give 5-nitro-3-trifluoromethyl-pyridin-2-ylamine (1.92 g, 75percent). 1H NMR (d6-DMSO, 300 MHz) δ 8.02 (brs, 2H), 8.38 (d, IH, J = 2.6 Hz), 9.04 (d, IH, J = 2.6 Hz); MS (ESI) m/z = 208 (MH+).
Reference: [1] Patent: WO2009/23179, 2009, A2, . Location in patent: Page/Page column 240-241
  • 9
  • [ 183610-70-0 ]
  • [ 79456-33-0 ]
YieldReaction ConditionsOperation in experiment
88% With N-chloro-succinimide In N,N-dimethyl-formamide at 60℃; for 1 h; Example 9 l-fl-fβf-dichlow-S-ftrifluowmethytyimidazofl^-aJpyridin^-ylJcarbonyl/^-piperidinyl)^- pyrrolidinone (Compound 110)Step A 5-chloro-3-(trifluoromethyl)-2-pyridinamine[0120] To a solution of 3-(trifluoromethyl)-2-pyridinamine (12.2 g, 75 mmol) in N5N- dimethylformamide (100 mL) was added N-chlorosuccinimide (10.5 g, 79 mmol). The mixture was heated to 60 0C and stirred for 1 hour. The reaction was allowed to cool to room temperature, concentrated, and the residue purified with a large silica plug, eluting with dichloromethane to give the title compound (13.0 g; 88percent). LCMS: m/z 197 (M+ 1).
88% With N-chloro-succinimide In N,N-dimethyl-formamide at 60℃; for 1 h; To a solution of 3-(trifluoromethyl)-2-pyridinamine (12.2 g, 75.2 mmol) in N,N-dimethylformamide (100 mL) was added N-chlorosuccinimide (10.55 g, 79.01 mmol). The mixture was heated to 60 °C and stirred for 1 hour. The mixture was allowed to cool to room temperature and was concentrated. The residue purified by passing through a silica plug, eluting with dichloromethane to give the title compound (13 g, 88percent). ES-LCMS m/z: 197, 199 (M+1 ).
Reference: [1] Patent: WO2010/91411, 2010, A1, . Location in patent: Page/Page column 88-89
[2] Patent: WO2011/41713, 2011, A2, . Location in patent: Page/Page column 206
[3] Patent: WO2015/79224, 2015, A1, . Location in patent: Page/Page column 60; 61
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 183610-70-0 ]

Fluorinated Building Blocks

Chemical Structure| 878804-93-4

[ 878804-93-4 ]

3-(Difluoromethyl)pyridin-2-amine

Similarity: 0.96

Chemical Structure| 79456-33-0

[ 79456-33-0 ]

5-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.87

Chemical Structure| 79456-34-1

[ 79456-34-1 ]

5-Bromo-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.85

Chemical Structure| 79456-27-2

[ 79456-27-2 ]

6-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.83

Chemical Structure| 106447-97-6

[ 106447-97-6 ]

2-Amino-4-(trifluoromethyl)pyridine

Similarity: 0.82

Amines

Chemical Structure| 878804-93-4

[ 878804-93-4 ]

3-(Difluoromethyl)pyridin-2-amine

Similarity: 0.96

Chemical Structure| 79456-33-0

[ 79456-33-0 ]

5-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.87

Chemical Structure| 79456-34-1

[ 79456-34-1 ]

5-Bromo-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.85

Chemical Structure| 79456-27-2

[ 79456-27-2 ]

6-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.83

Chemical Structure| 106447-97-6

[ 106447-97-6 ]

2-Amino-4-(trifluoromethyl)pyridine

Similarity: 0.82

Trifluoromethyls

Chemical Structure| 79456-33-0

[ 79456-33-0 ]

5-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.87

Chemical Structure| 79456-34-1

[ 79456-34-1 ]

5-Bromo-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.85

Chemical Structure| 79456-27-2

[ 79456-27-2 ]

6-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.83

Chemical Structure| 106447-97-6

[ 106447-97-6 ]

2-Amino-4-(trifluoromethyl)pyridine

Similarity: 0.82

Chemical Structure| 74784-70-6

[ 74784-70-6 ]

5-(Trifluoromethyl)pyridin-2-amine

Similarity: 0.78

Related Parent Nucleus of
[ 183610-70-0 ]

Pyridines

Chemical Structure| 878804-93-4

[ 878804-93-4 ]

3-(Difluoromethyl)pyridin-2-amine

Similarity: 0.96

Chemical Structure| 79456-33-0

[ 79456-33-0 ]

5-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.87

Chemical Structure| 79456-34-1

[ 79456-34-1 ]

5-Bromo-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.85

Chemical Structure| 79456-27-2

[ 79456-27-2 ]

6-Chloro-3-(trifluoromethyl)pyridin-2-amine

Similarity: 0.83

Chemical Structure| 106447-97-6

[ 106447-97-6 ]

2-Amino-4-(trifluoromethyl)pyridine

Similarity: 0.82